Synthetic studies on amphidinolide F: exploration of macrocycle construction by intramolecular Stille coupling

Decultot, L. and Clark, J. S. (2022) Synthetic studies on amphidinolide F: exploration of macrocycle construction by intramolecular Stille coupling. Organic Letters, 24(41), pp. 7600-7604. (doi: 10.1021/acs.orglett.2c03045) (PMID:36223230)

Abstract

Exploration of an ambitious new strategy for the total synthesis of the cytotoxic marine natural product amphidinolide F is described, which features fabrication of the core structure from four readily accessible fragments and macrocycle construction through C9–C10 bond formation by intramolecular Stille coupling between an alkenyl iodide and alkenyl stannane. Efficient stereoselective synthesis of each of the four building-blocks and subsequent coupling of them to produce the requisite cyclization precursor has been accomplished, but suitable conditions for high-yielding palladium-mediated closure of the macrocycle to produce the fully protected amphidinolide F ring system have yet to be identified.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Decultot, Ludovic
• Authors: Decultot, L., and Clark, J. S.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 12 October 2022
• Copyright Holders: Copyright © 2022 The Authors
• First Published: First published in Organic Letters 24(41): 7600-7604
• Publisher Policy: Reproduced under a Creative Commons License