Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

Yuki Fujishima, Yusuke Ogura, Ryo Towada, Masaru Enomoto, Shigefumi Kuwahara

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.

Original languageEnglish
Pages (from-to)5240-5242
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number47
DOIs
Publication statusPublished - 2016 Jan 1

Keywords

  • Amphidinolide
  • Cytotoxic
  • Macrolide
  • Partial synthesis
  • Polyketide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective synthesis of the C17–C29 fragment of amphidinolide N'. Together they form a unique fingerprint.

  • Cite this