Total synthesis, stereochemical reassignment, and biological evaluation of (-)-lyngbyaloside B

Haruhiko Fuwa, Yuta Okuaki, Naoya Yamagata, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


(-)-Lyngbyaloside B is a 14-membered macrolide glycoside isolated from the marine cyanobacterium Lyngbya sp. as a cytotoxic substance by Moore and co-workers. The first total synthesis of (-)-lyngbyaloside B and the reassignment of its stereostructure is described. The synthesis features an Abiko-Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alcohol. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.

Original languageEnglish
Pages (from-to)868-873
Number of pages6
JournalAngewandte Chemie - International Edition
Issue number3
Publication statusPublished - 2015 Jan 12


  • Aldol reactions
  • Macrolide glycosides
  • Natural products
  • Structure determination
  • Total synthesis


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