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Electroorganic synthesis, 57. Synthesis of advanced prostaglandin precursors by Kolbe electrolysis, II. – Preparation of coacids and anodic initiated tandem radical‐addition / radical‐coupling reaction with (1′ R ,4′ S ,3 R/S )‐3‐( cis ‐4‐acetoxycyclopent ‐2‐enyloxy)‐3‐ethoxypropionic acid
Author(s) -
Weiguny Jens,
Schäfer Hans J.
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940303
Subject(s) - chemistry , electrolysis , radical cyclization , silylation , tandem , prostaglandin , lactone , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , stereochemistry , catalysis , electrode , biochemistry , materials science , electrolyte , composite material
The α‐silyl‐substituted carboxylic acids 4 and 10 were prepared and with other coacids subjected to a mixed Kolbe electrolysis with β‐cyclopentenyloxypropanoate 1 . The stereochemical course of this cyclization reaction was determined on the basis of the 4‐methyl‐substituted product 23 by 1 H‐NMR‐NOE spectroscopy. Conversion of the bicyclic reaction products 21b–d to advanced prostaglandin precursors such as lactone 30 was achieved in few steps.