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

Man Ki Sit; Hui Hui Cao; Yan-Dong Wu; Tsz Chun Yip; Lars Eric Bendel; Wen Zhang; Wei-Min Dai

doi:10.1021/acs.orglett.3c00106

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

Org Lett. 2023 Mar 17;25(10):1633-1637. doi: 10.1021/acs.orglett.3c00106. Epub 2023 Feb 23.

Authors

Man Ki Sit¹, Hui Hui Cao², Yan-Dong Wu^{1

3}, Tsz Chun Yip¹, Lars Eric Bendel¹, Wen Zhang¹, Wei-Min Dai¹

Affiliations

¹ Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), and Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR P. R. of China.
² School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. of China.
³ College of Chemistry, Central China Normal University, Luoyu Road 152, Hongshan District, Wuhan 430079, Hubei, P. R. of China.

PMID: 36820513
DOI: 10.1021/acs.orglett.3c00106

Abstract

Synthesis of the C19-truncated maltepolide E has been accomplished via a diene-ene ring-closing metathesis (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 maltepolides A and B as proposed for the biosynthesis of maltepolides.