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Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction.

Abstract
[structure: see text] A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.
AuthorsShin-ichi Shirokawa, Mariko Shinoyama, Isao Ooi, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi
JournalOrganic letters (Org Lett) Vol. 9 Issue 5 Pg. 849-52 (Mar 1 2007) ISSN: 1523-7060 [Print] United States
PMID17288429 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Glycolipids
  • khafrefungin
Topics
  • Glycolipids (chemical synthesis, chemistry)
  • Molecular Structure
  • Stereoisomerism

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