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.

• Authors: Shin-ichi Shirokawa, Mariko Shinoyama, Isao Ooi, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi
• Journal: Organic letters (Org Lett) Vol. 9 Issue 5 Pg. 849-52 (Mar 01 2007) ISSN: 1523-7060 [Print] United States
• PMID: 17288429 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Glycolipids
• khafrefungin

Topics

• Glycolipids (chemical synthesis, chemistry)
• Molecular Structure
• Stereoisomerism