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

Zbigniew Pianowski; Leszek Rupnicki; Piotr Cmoch; Krzysztof Staliński

doi:10.1055/s-2005-864825

LETTER

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

Zbigniew Pianowski^a, Leszek Rupnicki^a, Piotr Cmoch^b, 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;

Abstract

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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.

Key words

bicyclic compounds - domino reactions - hydrides - natural products - radicals

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