Asymmetric synthesis of (+)-aspicilin

Chun Yi Wang, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Aspicilin (1), an eighteen membered macrolide with four stereocenters, was synthesized using (3R,4R)- 1,5-hexadiene-3,4-diol and (S)-propylene oxide as the starting materials. Sharpless epoxidation on the protected dienediol generated the required three consecutive stereocenters, and malonic ester synthesis added the acetyl unit. Yamaguchi protocol was applied to form the key ester with two terminal olefins ready for the ring-closing metathesis. RCM, hydrogenation, selenylation, oxidation and deprotections gave aspicilin with 4.7% total yield.

Original languageEnglish
Pages (from-to)389-393
Number of pages5
JournalJournal of the Chinese Chemical Society
Issue number3
StatePublished - Mar 2012


  • Aspicilin
  • Macrolide
  • Ring-closing metathesis


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