Preparation of a novel 16-DPA-P 2S 5 adduct and its application as a masked α,β-unsaturated ketone in [4+2]cycloaddition reactions

The reaction of 16-DPA with P 4S 10 in refluxing benzene afforded a novel adduct 16-DPA-P 2S 5 instead of the expected thione. The adduct undergoes [4+2]cycloaddition with alkyne dienophiles to afford steroidal (17,16- c)pyrans. Graphic

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 13; pp. 2741 - 2744
Main Authors Chetia, Apurba, Saikia, Anil, Saikia, Chandan J., Boruah, Romesh C.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2003
Subjects
16-Dehydropregnenolone acetate
[4+2]cycloaddition
steroidal (17,16- c)pyran
tetraphosphorous decasulfide
steroidal (17,16- c)pyran
[4+2]cycloaddition
16-Dehydropregnenolone acetate
tetraphosphorous decasulfide
Online AccessGet full text

Cover

More Information
Summary:The reaction of 16-DPA with P 4S 10 in refluxing benzene afforded a novel adduct 16-DPA-P 2S 5 instead of the expected thione. The adduct undergoes [4+2]cycloaddition with alkyne dienophiles to afford steroidal (17,16- c)pyrans. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00324-1