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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Short Communication

A Convergent Approach for Protected (+)-Paecilomycin F

Author(s): Ravi Gurram and Srihari Pabbaraja*

Volume 20, Issue 2, 2023

Published on: 15 August, 2022

Page: [185 - 192] Pages: 8

DOI: 10.2174/1570178619666220523094936

Price: $65

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).

Keywords: Macrolide, resorcylic acid lactone, metathesis, mitsunobu etherification, sharpless asymmetric dihydroxylation.

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