Annulation via donor-acceptor reagents. An efficient total synthesis of (±)-∆⁹⁽¹²⁾-capnellene

1 March 1984

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 62 (3) , 629-631
https://doi.org/10.1139/v84-600

Abstract

A short, efficient total synthesis of the racemic form of the marine sesquiterpenoid (-)-∆⁹⁽¹²⁾-capnellene (1) is described. The key steps of the synthesis are two methylenecyclopentane annulation sequences (14 → 16; 22 → 24) involving the CuBr-Me₂S→BF₃ • Et₂O catalyzed conjugate addition of the Grignard reagent 13 to the enones 14 and 22, followed by intramolecular alkylation (KH, tetrahydrofuran) of the resultant adducts 15 and 23, respectively

Keywords

TOTAL SYNTHESIS
EFFICIENT TOTAL
SUP
CATALYZED CONJUGATE
KEY STEPS
GRIGNARD REAGENT
MARINE SESQUITERPENOID
RACEMIC FORM

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Annulation via donor-acceptor reagents. An efficient total synthesis of (±)-∆9(12)-capnellene

Abstract

Keywords

Annulation via donor-acceptor reagents. An efficient total synthesis of (±)-∆⁹⁽¹²⁾-capnellene