Total synthesis of 14,21-diepi-squamocin-K

Chun Wei Liu, Tze Chiun Yeh, Chia Hsiu Chen, Chia Chun Yu, Cheng Sheng Chen, Duen Ren Hou, Jih Hwa Guh

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated.

Original languageEnglish
Pages (from-to)2971-2976
Number of pages6
JournalTetrahedron
Volume69
Issue number14
DOIs
StatePublished - 8 Apr 2013

Keywords

  • Annonaceous acetogenin
  • Asymmetric synthesis
  • C Symmetry
  • Cross metathesis
  • Ring-closing metathesis

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