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Nitro-olefin trapping reaction of enolatesin situgenerated by conjugate addition reaction: short syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI211 Prostaglandin Chemistry. XXXII. Part XXXI: T. Tanaka, N. Okamura, K. Bannai, A. Hazato, S. Sugiura, K. Tomimori, K. Manabe, and S. Kurozumi, Tetrahedron, in press.

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
43
Issue
5
Identifiers
DOI: 10.1016/s0040-4020(01)90018-3

Abstract

Abstract The nitro-olefin trapping of the enolates in situ generated by conjugate addition of organocopper reagents to the chiral oxygenated cyclopentenone synthon, R-4, gives the three-component coupling products in a regiospecific manner. The intermediary nitronate anion 17 is further transformed into the nitro compound or 6-oxo-PGE 1 ( 19) in a single pot. This coupling reaction is applicable to syntheses of naturally occurring prostaglandins such as PGE 1, 6-oxo-PGF 1α, and PGI 2.

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