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Total Synthesis of 3‐Hydroxydrimanes Mediated by Titanocene( III ) – Evaluation of Their Antifeedant Activity
Author(s) -
Justicia José,
Oltra J. Enrique,
Barrero Alejandro F.,
Guadaño Ana,
GonzálezColoma Azucena,
Cuerva Juan M.
Publication year - 2005
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/ejoc.200400634
Subject(s) - chemistry , total synthesis , surface modification , stereochemistry , organic chemistry , combinatorial chemistry
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)