Synthetic studies on taxol: Highly stereoselective construction of the taxol C-ring via S(N)2 ' reduction of an allylic phosphonium salt

The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereose...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 14; pp. 2973 - 2976
Main Authors Utsugi, Masayuki, Miyano, Masayuki, Nakada, Masahisa
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.07.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHIRAL BUILDING-BLOCKS
HYDRIDE REDUCTION
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Summary:The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S(N)2' reduction of the allylic phosphonium salts.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0608606