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Oxidative Enolate Cyclizations of 6,8‐Nonadienoates: Towards the Synthesis of Prostanes
Author(s) -
Jahn Ullrich,
Hartmann Philip,
Dix Ina,
Jones Peter G.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200202)2002:4<718::aid-ejoc718>3.0.co;2-6
Subject(s) - chemistry , oxidative phosphorylation , stereochemistry , biochemistry
6,8‐Nonadienoate enolates, which undergo radical 5‐ exo cyclization on SET oxidation with ferrocenium hexafluorophosphate, were studied as radical cyclization precursors. The trapping of the cyclized allylic radicals occurred with good regioselectivity through dimerization, TEMPO trapping, or SET oxidation/deprotonation reactions. 3‐Alkoxido enolates were chemoselectively oxidized to β‐oxy α‐carbonyl radical anions, which cyclized to produce functionalized cyclopentane derivatives. These cyclizations serve as a model study for the synthesis of prostaglandins and derivatives.