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

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

References and Notes

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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.