Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part I: Synthesis of the C1-C13 Subunit

Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Tsubasa Okano, Yasunobu Matsumoto, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Amphidinolide N, the structure of which has been recently revised, is a 26-membered macrolide featuring allyl epoxide and tetrahydropyran moieties with 13 chiral centers. Due to its challenging structure and extraordinary potent cytotoxicity, amphidinolide N is a highly attractive target of total synthesis. During our total synthesis studies of the 7,10-epimer of the proposed structure of amphidinolide N, we have synthesized the C1-C13 subunit enantio- and diastereoselectively. Key reactions include an l-proline catalyzed enantioselective intramolecular aldol reaction, Evans aldol reaction, Sharpless asymmetric epoxidation and Tamao-Fleming oxidation. To aid late-stage manipulations, we also developed the 4-(N-benzyloxycarbonyl-N-methylamino)butyryl group as a novel ester protective group for the C9 alcohol.

Original languageEnglish
Pages (from-to)3282-3286
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number10
DOIs
Publication statusPublished - Mar 1 2016
Externally publishedYes

Keywords

  • aldol reaction
  • organocatalyst
  • Sharpless epoxidation
  • Tamao-Fleming oxidation
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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