Nozaki-Kishi reaction of crotonates as a source of complex dienophiles: Application to the B-seco taxane series Journal Article

  


Authors: Queneau, Y.; Krol, W. J.; Bornmann, W. G.; Danishefsky, S. J.
Article Title: Nozaki-Kishi reaction of crotonates as a source of complex dienophiles: Application to the B-seco taxane series
Abstract: The Nozaki-Kishi coupling reaction between aldehyde 10 and 3-iodo-(E)-crotonate derivatives is used to produce functionalized allylic alcohols which served as precursors of highly substituted enones. Diels-Alder reactions of various dienophiles derived from this chemistry, with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene are described. In this way, highly oxygenated B-seco taxane derivatives are obtained in a concise fashion.
Keywords: diels-alder reaction; dienophiles; aldehydes; cycloaddition; diels-alder; acid; taxol; chloride; conversion; allylic alcohols; dienophile; halides; substructure; nozaki-kishi reaction; iodo olefin; iodo crotonate; chromium(ii); nickel(ii) chloride; organochromium; alpha-diketones; stereospecific hydrohalogenation reaction; chiral
Journal Title: Bulletin De La Societe Chimique De France
Volume: 130
Issue: 3
ISSN: 0037-8968
Publisher: Editions Scientifiques Elsevier  
Date Published: 1993-01-01
Start Page: 358
End Page: 370
Language: English
ACCESSION: WOS:A1993LM67200013
PROVIDER: wos
Notes: Article -- Source: Wos