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Total Synthesis of 3-Hydroxydrimanes Mediated by Titanocene(III) – Evaluation of Their Antifeedant Activity

✍ Scribed by José Justicia; J. Enrique Oltra; Alejandro F. Barrero; Ana Guadaño; Azucena González-Coloma; Juan M. Cuerva

Book ID
102178220
Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
142 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We describe the first synthesis of 3β‐hydroxydihydroconfertifolin (3) and 3β‐hydroxycinnamolide (4), together with improved procedures for the preparation of other 3‐hydroxydrimanes (2 and 5) scarce in nature. The key step was the titanocene(III)‐promoted cyclization of epoxypolyprenes, readily prepared from commercial polyenes. In this way, we confirm the viability of our procedure for the synthesis of drimane sesquiterpenoids with different functionalization patterns. We also report on the antifeedant activity of 2–5 against four insect species with different feeding ecologies. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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