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The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 and the unambiguous assignment of the C14 stereochemistry.

Authors :
Brummond KM
Sill PC
Chen H
Source :
Organic letters [Org Lett] 2004 Jan 22; Vol. 6 (2), pp. 149-52.
Publication Year :
2004

Abstract

[reaction: see text] The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 is reported. The highly unsaturated cyclopentenone prostaglandin was obtained via a silicon-tethered allenic [2 + 2 + 1] cycloaddition reaction developed in our group. In addition, the stereochemistry at C14 has been assigned unambiguously.

Subjects

Subjects :
Carbon chemistry
Cyclization
Molecular Structure
Silicon chemistry
Stereoisomerism
Prostaglandin D2 analogs & derivatives
Prostaglandin D2 chemical synthesis

Details

Language :
English
ISSN :
1523-7060
Volume :
6
Issue :
2
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
14723515
Full Text :
https://doi.org/10.1021/ol035590v
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