Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy-Reference-Cited by-同舟云学术

Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy

Published:2021-10-28 Issue: Volume: Page:
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Author:

Sit Man Ki¹,Cao Hui Hui²,Wu Yan-Dong¹,Yip Tsz Chun¹,Bendel Lars Eric¹,Zhang Wen¹,Dai Wei-Min¹^ORCID

Affiliation:

1. Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and Department of Chemistry, The Hong Kong University of Science and Technology, Hong Kong SAR, P. R. of China

2. School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. of China

Abstract

Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene RCM strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring-opening to furnish the C19-truncated maltepolide A and B as proposed for the biosynthesis of maltepolides. Preliminary cytotoxicity data of the synthesized C19-truncated maltepolides against L929 mouse fibroblast cell line suggest irrelevance of the vinyl epoxide and importance of the conjugated dienyl keto unit for the observed anticancer activity.

Publisher

American Chemical Society (ACS)

Link

https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/6179fc62ff3ba95dc7a5ff35/original/synthesis-of-the-macrolactone-cores-of-maltepolides-via-a-diene-ene-ring-closing-metathesis-strategy.pdf

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1. Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy;Organic Letters;2023-02-23