Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis

Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Kenji Harada, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.

Original languageEnglish
Pages (from-to)3287-3291
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number10
DOIs
Publication statusPublished - 2016 Mar 1

Keywords

  • Enders RMAP
  • Grieco-Nishizawa olefination
  • Keck allylation
  • Shi-epoxidation
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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