Organic Chemistry

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

Authors

  • Man Ki Sit 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 ,
  • Hui Hui Cao School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. of China ,
  • Yan-Dong Wu 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 ,
  • Tsz Chun Yip 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 ,
  • Lars Eric Bendel 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 ,
  • Wen Zhang 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 ,
  • Wei-Min Dai 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

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.

Content

Thumbnail image of Maltepolide_Core_dai_v1.pdf

Supplementary material

Thumbnail image of SI-dai_v1.pdf
Supporting Information
Comparison of 13C NMR data of compounds 50 and 51 with maltepolide A and B and copies of 1H and 13C spectra of compounds 48–51.