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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,3R/S)-3-(cis-4-acetoxycyclopent -2-enyloxy)-3-ethoxypropionic acid

✍ Scribed by Weiguny, Jens ;Schäfer, Hans J.

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 821 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419940303

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✦ Synopsis

Abstract

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. magnified image

📜 SIMILAR VOLUMES

Electroorganic synthesis, 56. Synthesis

Electroorganic synthesis, 56. Synthesis of advanced prostaglandin precursors by Kolbe electrolysis, I. – Preparation of (1′R,4′S,3RS)-3-(cis-4-acetoxycyclopent-2-enyloxy)-3-ethoxypropionic acid

✍ Weiguny, Jens ;Schäfer, Hans J. 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 964 KB

## Abstract The key intermediate of a novel synthesis of prostaglandin precursors, (1′__R__,4′__S__,3__R__/__S__)‐3‐(__cis__‐4‐acetoxycyclopent‐2‐enyl oxy)‐3‐ethoxypropionic acid (3), is prepared by two different synthetic sequences: In a first strategy transacetalization of ethyl 3,3‐diethoxypropi