Tetrahedron Letters

A novel approach toward the synthesis of strigolactones through intramolecular [2+ 2] cycloaddition of ketenes and ketene-iminiums to olefins. Application to the …

M Lachia, PMJ Jung, A De Mesmaeker

Index: Lachia, Mathilde; Jung, Pierre M.J.; De Mesmaeker, Alain Tetrahedron Letters, 2012 , vol. 53, # 34 p. 4514 - 4517

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Citation Number: 21

Abstract

An intramolecular [2+ 2] cycloaddition of ketenes and ketene-iminium was developed for the preparation of GR-24, a synthetic analogue of the family of strigolactone plant hormones. Excellent levels of regioselectivity and of chiral induction were obtained using a bulky chiral amine for the formation of the cyclobutanone and a subsequent regioselective Baeyer– Villiger afforded the tricyclic lactone core of (+)-GR-24.