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Synlett 2010(5): 793-795  
DOI: 10.1055/s-0029-1219381
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Conjugate Addition of Crotylstannane: Synthesis of (-)-Lasiol

Emily E. Wilding, John J. Gregg, Richard J. Mullins*
Department of Chemistry, Xavier University, 3800 Victory Parkway, Cincinnati, OH 45207-4221, USA
Fax: +1(513)7453695; e-Mail: mullinsr@xavier.edu;
Further Information

Publication History

Received 29 September 2009
Publication Date:
08 February 2010 (online)

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Abstract

Lasiol, the major component of the mandibular gland secretion, serves as the primary sex attractant of the male ant, Lasius meridionalis. Our interest in lasiol stems from the stereochemistry of the chiral methyl substituents and the synthetic challenges posed by this common structural motif. As such, an asymmetric 1,4-conjugate addition of an allylic stannane to produce the 1,2-anti-dimethyl arrangement with high stereocontrol has resulted in the synthesis of (-)-lasiol.

Key words

asymmetric synthesis - 1,4-addition - (-)-lasiol - chiral auxiliaries - Lewis acids

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19

The relative and absolute stereochemistry of the major product 4 was proven via X-ray crystallography, see ref. 16.

20

Similar endgame has been utilized in previous lasiol syntheses, see ref. 1 and 2.