Synlett 2005(6): 0900-0904  
DOI: 10.1055/s-2005-864825
LETTER
© Georg Thieme Verlag Stuttgart · New York

Radical Cyclizations Leading to the Bicyclo[2.2.1]heptane Framework: A New Radical Approach to (±)-(Z)-β-Santalol

Zbigniew Pianowskia, Leszek Rupnickia, Piotr Cmochb, Krzysztof Staliński*b
a Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
b Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: stalinsk@icho.edu.pl;
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Publikationsverlauf

Received 28 August 2004
Publikationsdatum:
23. März 2005 (online)

Abstract

Tandem radical cyclizations of acyclic iodides, including [3-(2-iodoethyl)-6,10-dimethyl-undeca-5,9-dien-1-ynyl]-dimethyl­phenylsilane lead in good yields to bicyclo[2.2.1]heptane derivatives. The cascade relies on two sequential radical-mediated 5-exo-cyclizations. The radical approach is illustrated with the total ­synthesis of racemic-(Z)-β-santalol. The results are remarkable, two fused rings and one stereogenic center are formed in a single operation. A new ‘coordinated’ hydride appeared to be useful in the ­cascade.