Total Synthesis of Khafrefungin Using Highly Stereoselective Vinylogous Mukaiyama Aldol Reaction

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 Mit...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 5; pp. 849 - 852
Main Authors Shirokawa, Shin-ichi, Shinoyama, Mariko, Ooi, Isao, Hosokawa, Seijiro, Nakazaki, Atsuo, Kobayashi, Susumu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Glycolipids - chemical synthesis
Glycolipids - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
OXIDATION
ALCOHOLS
STRUCTURAL DETERMINATION
RUSTMICIN
SPHINGOLIPID SYNTHESIS
1ST TOTAL-SYNTHESIS
DEPROTECTION
SACCHAROMYCES-CEREVISIAE
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0630191