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A Total Synthesis of (±)-9-Pupukeanone

✍ Scribed by Piers, Edward ;Winter, Manfred

Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
730 KB
Volume
1982
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

A stereoselective total synthesis of (±)‐9‐pupukeanone (3), an intermediate employed in previously reported total syntheses of the structurally novel sesquiterpenoid (±)‐9‐isocyanopupukeanane (1), is described. In the key step of the synthetic sequence, the epimeric mixture of allylic alcohols 15, obtained in 7 steps from 4,6‐dimethyl‐1,3‐cyclohexanedione (6), underwent a smooth intramolecular Diels‐Alder reaction, providing in high yield the tricyclic alcohols 18 (mixture of epimers). The latter material was converted via a 5‐step sequence into (±)‐9‐pupukeanone (3).

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.