Diyl Trapping Reactions To Synthesize Taxol Analogs

A new and efficient entry to the ABC-ring system common to taxol and related materials has been developed. Highlights include the use of a regioselective intramolecular diyl trapping reaction to synthesize tricyclic alkene 5, the creation and oxidative cleavage of the tetrasubstituted olefin found i...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 6; pp. 1610 - 1616
Main Authors Ott, Michael M, Little, R. Daniel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.03.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RING-SYSTEM
COMPLETION
CONSTRUCTION
C-RING
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Summary:A new and efficient entry to the ABC-ring system common to taxol and related materials has been developed. Highlights include the use of a regioselective intramolecular diyl trapping reaction to synthesize tricyclic alkene 5, the creation and oxidative cleavage of the tetrasubstituted olefin found in ketal 20a,b to afford a highly functionalized eight-membered ring (21a), and cyclization of 22, thereby providing the tricyclic core.
Bibliography:ark:/67375/TPS-2F1CLNCX-9
istex:5769211A817841CAB0D456CF4762A0881FBE02DD
Abstract published in Advance ACS Abstracts, March 1, 1997.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo970042e