Convergent synthesis of the C1-C29 framework of amphidinolide F

Romiti, F., Decultot, L. and Clark, J. S. (2022) Convergent synthesis of the C1-C29 framework of amphidinolide F. Journal of Organic Chemistry, 87(12), pp. 8126-8141. (doi: 10.1021/acs.joc.2c00850) (PMID:35675580) (PMCID:PMC9207912)

Abstract

The complete carbon framework of the macrocyclic marine natural product amphidinolide F has been prepared by a convergent synthetic route in which three fragments of similar size and complexity have been coupled. Key features of the syntheses of the fragments include the stereoselective construction of the tetrahydrofuran in the C1–C9 fragment by oxonium ylide (free or metal-bound) formation and rearrangement triggered by the direct generation of a rhodium carbenoid from 1-sulfonyl-1,2,3-triazole, the highly diastereoselective aldol reaction between a boron enolate and an aldehyde with 1,4-control to prepare the C10–C17 fragment, and the formation of the tetrahydrofuran in the C18–C29 fragment by intramolecular nucleophilic ring opening of an epoxide with a hydroxyl group under acidic conditions.

• Item Type: Articles
• Additional Information: The authors thank Dr. Ian Sword for generously providing full financial support to L.D. during his Ph.D.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Decultot, Ludovic
• Authors: Romiti, F., Decultot, L., and Clark, J. S.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Published Online: 08 June 2022
• Copyright Holders: Copyright © 2022 The Authors
• First Published: First published in Journal of Organic Chemistry 87(12):8126-8141
• Publisher Policy: Reproduced under a Creative Commons License