Affiliation:
1. Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad
500007, India
Abstract
Background:
A stereoselective synthetic strategy toward (+)-paecilomycin F is reported.
The approach utilizes readily available commercial 2,4,6-trihydroxy benzoic acid and easily accessible
chiral R(+)-propylene oxide as starting materials.
Methods:
The synthesis involves regioselective Grignard reaction, Wittig reaction, Sharpless asymmetric
dihydroxylation, Barbier-type allylation, Stille-coupling and ring-closing metathesis as key reactions.
Results:
The target molecule is produced in a 7-step linear sequence with an overall yield of 20% starting
from 2,4,6-trihydroxy benzoic acid or a 12-step sequence with an overall yield of 12.95% starting
from R(+)-propylene oxide.
Conclusion:
The aromatic fragment synthesis was achieved using earlier known protocols starting
from 2,4,6-trihydroxy benzoic acid (vide infra).
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry