chapter 30 — retrosynthetic analysis planning a synthesis by going
TRANSCRIPT
Chapter 30 — Retrosynthetic analysis
Planning a synthesis by going in reverse
I can make that! C–C disconnections from familiar reactions
Example: a return to platensimycin
Example: monensin
I can make that! (C–C disconnections 1.)
OHO
OO
OHOH OHO
O O
O O
O
RO
OClaisen
1 32
1 32
1 32
aldol
aldol[Red.]
[Red.]
1,3 - O,O
O OHO O Oaldolα,β
Elim.
I can make that! (C–C disconnections 2.)
R
OHN
1 32
1,3 - N,O
R' R'
R
ONR' R'O
R H
ONH
R' R'
Mannich[Red.]
1,5 - O,OO
O
OR
O
O
ORMichael
HO OH
R R'[Red.]
O O
R R'Michael
O
R
O
R'
1 32
45
1 32 54
Monensin: How on earth?
Monensin: How on earth?
Monensin: How on earth?