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Tetrahedron Letters Vol. 53, Issue 44, 2012

Contents

COMMUNICATIONS

New potent vinca alkaloids resulting from an unexpected isomerization pp 5821–5823

Quoc Anh Ngo, Fanny Roussi*, Sylviane Thoret, Françoise Guéritte

Synthesis and resolution of a new thiahexahelicene pp 5824–5827

Souad Moussa, Faouzi Aloui, Béchir Ben Hassine*

Donnazoles A and B from Axinella donnani sponge: very close derivatives from the postulated intermediate‘pre-axinellamine’

pp 5828–5832

Julie Muñoz*, Céline Moriou, Jean-François Gallard, Pierre Daniel Marie, Ali Al-Mourabit

5809

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Tetrahedron Letters

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Efficient and scalable synthesis of thiazole fused benzazepine as a D2 partial agonist pp 5833–5836

Hui Xiong*, Ye Wu, Scott G. Lehr, William Blackwell, Gary Steelman, Jim Hulsizer, Rebecca A. Urbanek

4 steps

1

30%NH N

S

NH2N

NN

2

The development of an efficient and scalable synthetic route to prepare the selective D2 partial agonist (1) is described here. Regioselective nitration of tetrahydrobenzazepine 2,followed by reductive amination, hydrogenation, and oxidative cyclization afforded 1 in good yield, without the need of column chromatography.

Concise syntheses of three x-3 polyunsaturated fatty acids pp 5837–5839

Martin Gjerde Jakobsen, Anders Vik, Trond Vidar Hansen*

Synthesis of 3,4-dihydropyridin-2-one derivatives in convergent mode applying bio catalyst vitamin B1 andpolymer supported catalyst PEG–SO3H from two different sets of building blocks

pp 5840–5844

Koyel Pradhan, Pranabes Bhattacharyya, Sanjay Paul, Asish R. Das*

CHO

CN

CONH2

VB1, H2O, 100 oC

NH

O

NO2

CNONO2

CN

CNH2O ,100 oC

O

OPEG SO3H,

+

Convenient syntheses of novel 1-isothiocyano-alkylphosphonate diphenyl ester derivatives with potentialbiological activity

pp 5845–5847

Mateusz Psurski, Marta Piguła, Jarosław Ciekot, Łukasz Winiarski, Joanna Wietrzyk, Józef Oleksyszyn*

O P

3R' H

OO NH2

O

O NH

O

P

R'O

O

O

H2N P

R'O

O

O

HBrSCN P

R'O

O

O

HBF4/MeCN

33% HBr/AcOHCS2/DIPEA/HBTU/DMForCS2/Et3N/H2O2/DMF

5810 Contents / Tetrahedron Letters 53 (2012) 5809–5819

A turn-on Schiff base fluorescence sensor for zinc ion pp 5848–5851

Wei Hsun Hsieh, Chin-Feng Wan, De-Jhong Liao, An-Tai Wu*

N NN

OH

HON

HO

N NN

O

ON

OZn2+

Zn2+

Buffer and sugar concentration dependent fluorescence response of a BODIPY-based aryl monoboronic acidsensor

pp 5852–5855

J. S. Hansen*, J. F. Petersen, T. Hoeg-Jensen, J. B. Christensen

500 550 6000.0

0.5

1.0

Increased [D-glc]

wavelength (nm)

If

Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D pp 5856–5858

Prakash R. Sultane, Amar R. Mohite, Ramakrishna G. Bhat*

NCbz OH

HOMe

O

NOH

OHOH

HN

OHH

Pumiliotoxin 251D1-deoxy-7,8a-di-epi-castanospermine

***

An efficient and highly selective approach for the construction of novel dispiro heterocycles inguanidine-based task-specific [TMG][Ac] ionic liquid

pp 5859–5863

Anshu Dandia*, Anuj K. Jain, Sonam Sharma

NR

ArH

ArH

H3C

HN COOH

N

Ar

R

N

H

Ar

O

O

CH3

O

(1a-l)

+

4a-l

N

Ar

R

N

H ArO

H3C

O

O

O

O

O

OH

OH

5a-l

2 3

+

[TMG][Ac]

80°C

Contents / Tetrahedron Letters 53 (2012) 5809–5819 5811

Cleavage of ring A and formation of an unusual nor-triterpene skeleton via the Baeyer–Villiger reaction pp 5864–5867

Özgür Tag, Ali Çagır, Ikhlas A. Khan, Erdal Bedir*

A new, facile, and protection-free one-pot chemical synthesis of 20-deoxynucleoside-50-tetraphosphates pp 5868–5870

Anilkumar R. Kore*, Annamalai Senthilvelan, Muthian Shanmugasundaram

BO

OH

OPOO

POO

POO

POO

O O OO

B = G, A, C, T

A DFT study of the origins of the stereoselectivity in the aldol reaction of bicyclic amino ketones in thepresence of water

pp 5871–5874

Ryszard Lazny*, Artur Ratkiewicz, Aneta Nodzewska, Joanna Wysocka

N

O OH

Me

H

(CH2)n

N

O

Me (CH2)n

H2O, rt

n = 2, 3 exo, syn

R

exo, anti

N

O OH

Me

H

(CH2)n

R

?

CHO

R

H2O, rt?

CHO

R

Fluorometric sensing of Cu2+ ion with smart fluorescence light-up probe, triazolylpyrene (TNDMBPy) pp 5875–5879

Subhendu Sekhar Bag*, Rajen Kundu, Sangita Talukdar

-200

200

600

1000

1400

1800

Na(I) K(I) Mg(II) Ca(II) Co(II) Ni(II) Cu(I) Cu(II) Zn(II) Ag(I)

(I –

I 0)/I

0x

100%

0

100000

200000

300000

400000

350 450 550 650Wavelength (nm)

Inte

nist

y (a

. u.)

We report the detection of Cu2+ ion with fluorescence light-up probe, triazolylpyrene (TNDMBPy). Thus, the probe showed a remarkable fluorescenceenhancement of both the monomer and excimer emissions and a 2:1 probe–Cu2+ complexation with high selectivity and stability constant. Our probe isalso capable of sensing SDS micelle-encapsulated-Cu2+ ion in aqueous media proving its potential practical utility. Formation of the excimer was alsorationalized on the basis of DFT calculation.


Modified Markó’s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygenat room temperature

pp 5880–5882

Takeshi Nishii, Tomomi Ouchi, Aya Matsuda, Yuka Matsubara, Yuuko Haraguchi, Tomomi Kawano, Hiroto Kaku,Mitsuyo Horikawa, Tetsuto Tsunoda*

aldehyde

ketoneoralcohol

Air or O2, Tol, r.t.

CuCl / dpPhen (10 mol %)DBAD (10 mol %)

Cs2CO3 (200 mol %)

N NCO2

tBu

tBuO2CDBAD

N N

dpPhen

PhPh

A new synthesis of 2-aryl/alkylbenzofurans by visible light stimulated intermolecular Sonogashira couplingand cyclization reaction in water

pp 5883–5886

Somnath Ghosh*, Jhantu Das, Forid Saikh

O Ar/ R1

R[Pd] / ligand / Et3N

OH

XRAr/ R1+

H2O, visible light

X = Br, I

Synthesis, characterization, and X-ray analysis of new N,N0-disubstituted-1,4-diazepanes pp 5887–5890

Pedro I. Ramirez-Montes, María Eugenia Ochoa, Vianey Rodríguez, Rosa Santillan*, Héctor García-Ortega,Patricia Rodríguez, Norberto Farfán

Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM andPOM groups for probing RNA catalysis

pp 5891–5894

Shinya Harusawa*, Hiroki Yoneyama, Daiki Fujisue, Masayoshi Nishiura, Mihoyo Fujitake, Yoshihide Usami,Zheng-yun Zhao, Scott A. McPhee, Timothy J. Wilson, David M. J. Lilley

ODMTO

O

(CH2)n

NN

NN

PiPr2N

ONC

OR2

1a : n = 0, R1= MeR2 = CH2CH2CN

1b : n = 2, R1 = HR2 = TBDMS

O

R1 O

OO

O

(CH2)n

NN

NNH

P

OH

OO

O

G638VSCnTez


Stereoselective total synthesis of the E-isomer of putative lucentamycin A pp 5895–5898

Khalid B. Selim, Baeck Kyoung Lee, Taebo Sim*

NO

HN

NH

O

HO

O

HN NH2

NH

Ph

ONHO

Boc

6 (2S,3R,E) E-1a

NHO

BocN

HO

Boc

5a (2S,3R,Z)4a

alkeneinversionRh-catalyzed

reductivecyclization

Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction ofunsaturated imines

pp 5899–5902

Katsunori Tanaka*, Eric R. O. Siwu, Shinji Hirosaki, Takayuki Iwata, Risa Matsumoto, Yasutaka Kitagawa, Ambara R. Pradipta,Mitsutaka Okumura, Koichi Fukase*

BnNH2

rt, 5h

O

R2

H

N

NRN

Bn

Bn R2

R2

R1

R1

R1

N

R2

H

R1

Bn

N

R2

H

R1

Bn

RNH2

[4+4] Mediator

Double nucleophilic N-alkylation of a-oxime-esters with Grignard reagents pp 5903–5906

Yusuke Mizutani, Hiroki Tanimoto*, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi*

Preparation of dibromopyridines having –(CH2)m–SO3Na groups as monomers for new polypyridines pp 5907–5910

Tohru Takei, Takumi Ohki, Yosuke Harada, Naoto Kumagai, Hiroki Fukumoto, Take-aki Koizumi, Akihiro Maeda,Takahiro Kojima, Yoshihisa Sei, Kohei Shiramizu, Masahiro Abe, Masashi Oota, Takakazu Yamamoto*

NBr Br

O 2 SO3Na4

NBr

NH HN

Br

SO3NaNaO3S

CH


Cooperative perfunctionalization and partial labeling of 6-azido-6-deoxy-a-cyclodextrin through copper(I)-catalyzedazide–alkyne cycloaddition

pp 5911–5915

Geon-Hi Park, Jong Mun Baek, Hoa Thi Le, Choon Woo Lim*, Tae Woo Kim*

O

HOOH

N3

O

HO

HO

N3

O

OH

HON3

O

OHHO

N3

O

OH

OOH

N3

O

HO

OHN3

O

O

O

O

OO

HOOH

N

N

N

OH

O

HO

HO

N

NN

O

OH

HON N

N

HO

O

OHHO

N

N

N

HO

O

OH

OOH

N

N N

HO

O

HO

OHNN

N

OH

O

O

O

O

O

O

HO

O

COOH

HN

O

O

XStepwise

One-Pot

Partial FluoresceinLabeling by CuAAC

Fluorescent properties of coumarins with dual functions constructed by two sequential reactions pp 5916–5919

Tomoya Hirano, Haruko Kubo, Takuya Shiraishi, Kenichi Hiromoto, Takashi Fujiwara, Hiroyuki Kagechika*

Total synthesis of the COPD biomarker desmosine via Sonogashira and Negishi cross-coupling reactions pp 5920–5922

Hiroto Yanuma, Toyonobu Usuki*

Thiamine hydrochloride (VB1) as an efficient promoter for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones

pp 5923–5925

Yijia Chen, Weiguang Shan, Min Lei*, Lihong Hu*

up to 94% yield

RefluxVB1

EtOH

R1 CHO

NH

O

O

O

NH4OAc+

NH

NH

O

R1

+X X


A facile approach to the synthesis of securinega alkaloids: stereoselective total synthesis of ())-allonorsecurinine pp 5926–5928

Alugubelli Sathish Reddy, Pabbaraja Srihari*

NH

OH

O

HN

OO

(-)-Allonorsecurinine

H

10 StepsL(-)-Proline

Serendipitous synthesis of 3-hydroxy tetrahydrofurans from tin catalyzed sulfonylation of acyclic 1,2,4-triols pp 5929–5932

Makhosazana P. Gamedze, Rejoice B. Maseko, Fidelis Chigondo, Comfort M. Nkambule*

OTsOH

OHOHOH

p-TsCl, Et3N, Bu2SnO

CH2Cl2, reflux, 3.5 h

5-12%

O

OH

OH

66-83%

+

R

R

R

O

OH

OHOHOH

56-85%

R R

A cascade transformation of the cyclic form of a formylamino derivative of the alicyclic 1,5,9-triketone, 2,6-bis[(2-oxocyclohexyl)methyl)]cyclohexanone

pp 5933–5935

Taisia I. Akimova*, Natalia S. Kravchenko, Andrey V. Gerasimenko, Vladimir A. Denisenko, Vladimir I. Vysotskii

N

O

CHOO

CHO

NH OHN

O

conc. HCl O2

Al2O3

hexane,

Temporary thio-derivatization in the synthesis of (+)-4-acetylbromoxone pp 5936–5938

Aisling O’Byrne, Steven O’Reilly, Catherine Tighe, Paul Evans*, Laura Ciuffini, M. Gabriella Santoro

O

OHSR

O

OTBS

O

OAc

OBr

5 Steps

(1) EKR;(2) Silylation-Elimination

(±) ( ) (+)


Synthesis, characterization, and properties of 7,70-bis(3,6-di-tert-butylcarbazol-N-yl)-substituted fluorenyl-oligothiophenes

pp 5939–5943

Janeeya Khunchalee, Ruangchai Tarsaeng, Siriporn Jungsuttiwong, Tinnagon Keawin, Taweesak Sudyoadsuk, Vinich Promarak*

BCFTn(n = 0, 2, 4, 6, 8)

N

C6H13

t-Bu

t-Bu

C6H13

S N

t-Bu

t-Bu

C6H13 C6H13n

A phosphoryl to spiro-bicyclophosphorane transformation via b-amidic proton elimination in phosphorylatedhydrazides

pp 5944–5947

Khodayar Gholivand*, Hamid R. Mahzouni, Foroogh Molaei, Ali A. Kalateh

P

O

HN NH

RNN

C OPh

H

C

Ph

O

αβ

cyclization

O

P N

N

O

N

N H

H

R

Ph

Ph

H

- H2O

The tetrahedral phosphoryl structure is transformed into a spiro-bicyclophosphorane system with trigonal bipyramidal geometry by the elimination of ab-amidic proton in the reaction between a hydrazide and phosphoryl reagents with at least two leaving groups (Cl) bound to the phosphorus atom, suchas POCl3 or PhPOCl2.

A convenient method for the preparation of mono- and bis-substituted photochromicbis(benzothienyl)perfluorocyclopentenes via regioselective Friedel–Crafts acylation

pp 5948–5951

A. M. Bogacheva*, V. N. Yarovenko, K. S. Levchenko, O. I. Kobeleva, T. M. Valova, V. A. Barachevsky, M. I. Struchkova,P. S. Shmelin, M. M. Krayushkin, V. N. Charushin

S

F

FF F

F

F

S S

F

FF F

F

F

SS

F

FF F

F

F

SRR R

S

F

FF F

F

F

SRR

S

F

FF F

F

F

SR

hv hv' hv hv'R= C(O)CH2Br, Het, C(O)Het

hv

hv'

Stereoselective synthesis of methyl branched chiral deoxypropionate units: a new route for synthesis of insectpheromone ())-lardolure and (2R,4R,6R,8R) 2,4,6,8-tetramethylundecanoic acid

pp 5952–5954

J. S. Yadav*, Sandip Sengupta, Nagendra Nath Yadav, D. Narasimha Chary, Ahmad Alkhazim Al Ghamdi

OCHO

COOH

(-)-Lardolure (1)

(2R,4R,6R,8R)-2,4,6,8-tetramethyl undecanoic acid (2)

OHOAc OH

8 9 10OH OTBS


Novel sequential 1,4-Brook rearrangement–Wittig reaction: new one-pot approach for silyl dienol ethers pp 5955–5957

Yuji Matsuya*, Azusa Koiwai, Daishiro Minato, Kenji Sugimoto, Naoki Toyooka

Catalyst-free ipso-nitration of aryl boronic acids using bismuth nitrate pp 5958–5960

Rammohan R. Yadav, Ram A. Vishwakarma*, Sandip B. Bharate*

0.410 mmol

0.840 mmol Bi(NO3)3. 5 H2O

Toluene or BenzeneAr B(OH)2 Ar NO2

Ar = aryl, heteroaryl70-80 oC, 1.5 - 2 h, N2 atm.

"Catalyst-free"

A simple and efficient ‘catalyst-free’ ipso-nitration of aryl boronic acids using bismuth (III) nitrate as a nitrating agent is described.

Catalytic application of dinuclear palladium(II) bis(thiosemicarbazone) complex in the Mizoroki-Heck reaction pp 5961–5965

Rupesh Narayana Prabhu, Rengan Ramesh*

X

R+

R1

R

R1

Square planar dinuclear palladium(II) terephthaldehyde bis(thiosemicarbazone) complex was synthesized and characterized. The new complex acts as aneffective homogeneous catalyst for the Mizoroki-Heck reaction of aryl halides with various olefins. The effects of base, solvent, reaction temperature andcatalyst loading on the catalytic activity of the complex were also investigated.

OTHER CONTENTS

Corrigendum p 5966

Corrigendum p 5967


*Corresponding authorSupplementary data available via SciVerse ScienceDirect

Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�

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ISSN 0040-4039


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