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Radical cyclization strategies to terpenoids; syntheses of (±)-β-cuparenone, (±)-laurene and epilaurenes

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
47
Issue
3
Identifiers
DOI: 10.1016/s0040-4020(01)90504-6

Abstract

Abstract Radical cyclization of the bromide 8 , obtained in 5 steps from the ketone 9 , furnished exclusively 14 via 6-endo trig cyclization with out any observable amount of 5-exo trig product 1 . 5-Exo dig radical cyclizatlon of the bromo acetate 23 , prepared from 18 via the aldehyde 21 , followed by routine transformations furnished the cyclopentenone 26 , an immediate precursor to β-cuparenone ( 2 ). Similarly, total synthesis of laurenes 4 and 5 was achieved via the 5-exo dig radical cyclization of the xanthate 28 , obtained from the aldehyde 21 .

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