a practical synthetic route to pancratistatins**juan carlos ortiz,† lidia ozores,‡ fernando...
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![Page 1: A Practical Synthetic Route to Pancratistatins**Juan Carlos Ortiz,† Lidia Ozores,‡ Fernando Cagide, Ricardo Alonso* Departamento de Química Orgánica, Universidade de Santiago,](https://reader035.vdocuments.net/reader035/viewer/2022071607/6145427834130627ed50dd04/html5/thumbnails/1.jpg)
Annulation of β-aryl-α-nitro-α,β−enals and 2,2-dimethyl-1,3-dioxan-5-one: a one-step
assembly of nitrocyclitols. Application to a short practical synthesis of (+/-)-7-deoxy-2-
epi-pancratistatin tetraacetate
Juan Carlos Ortiz,† Lidia Ozores,‡ Fernando Cagide, Ricardo Alonso*
Departamento de Química Orgánica, Universidade de Santiago, 15782 Santiago de Compostela, Spain
Supporting Information qoraa@u
† Currently at Sintenovo, Mexico. ‡ Currently at the Max Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
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ppm (f1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
O
H
S2
![Page 3: A Practical Synthetic Route to Pancratistatins**Juan Carlos Ortiz,† Lidia Ozores,‡ Fernando Cagide, Ricardo Alonso* Departamento de Química Orgánica, Universidade de Santiago,](https://reader035.vdocuments.net/reader035/viewer/2022071607/6145427834130627ed50dd04/html5/thumbnails/3.jpg)
ppm (f1)050100150200
NO2
OH
OO
O
H
O
S3
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ppm (t1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
HO
O
S4
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ppm (t1)050100150200
O
O NO2
OH
OO
OH
S5
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ppm (t1)050100150200
NO2
OH
OO
O
HO
O
S6
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ppm (f1)0.01.02.03.04.05.06.07.08.0
O
O NO2
OH
OO
OH
OMe
S7
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ppm (t1)050100150200
NO2
OH
OO
O
HO
O
OMe
S8
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ppm (t1)050100150200
NO2
OH
OO
O
HO
O
OMe
S9
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ppm (t1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
H
O
S10
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ppm (t1)050100150200
NO2
OH
OO
O
H
O
S11
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ppm (f1)050100150200
NO2
OH
OO
O
H
O
S12
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ppm (t1)0.01.02.03.04.05.06.07.08.0
HNO
OO
O
HO
OO
MeO
S13
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ppm (t1)050100150200
HNO
OO
O
HO
OO
MeO
S14
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ppm (t1)050100150200
HNO
OO
O
HO
OO
MeO
S15
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ppm (t1)0.01.02.03.04.05.06.07.08.0
HNOAc
OAcOAc
AcO
HO
OO
MeO
S16
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ppm (t1)050100150200
HNOAc
OAcOAc
AcO
HO
OO
MeO
S17
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ppm (t1)050100150200
HNOAc
OAcOAc
AcO
HO
OO
MeO
S18
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ppm (t1)1.02.03.04.05.06.07.08.0
NHOAc
OAcOAc
AcO
HO
O
O
S19
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ppm (t1)050100150200
NHOAc
OAcOAc
AcO
HO
O
O
S20
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ppm (t1)050100150200
NHOAc
OAcOAc
AcO
HO
O
O
S21