Short New Route to the Chiral Spiro‐Tetrahydrofuran Subunit Common to Some Terpenoids

Abstract

Synthetic strategy based on a stereoselective iodoetherification reaction of a carvone‐derived hydroxyalkene unit has been developed for the asymmetric synthesis of the key spiro‐tetrahydrofuran subunit common to some naturally occurring terpenoids.

Keywords:

• Spirocycle
• carvone
• Barbier reaction
• iodoetherification
• terpenoid

Acknowledgment

Financial assistance from Council of Scientific and Industrial Research (CSIR), New Delhi (Grant No. 01/1676/00/EMR‐II) is gratefully acknowledged. One of the authors (S. K. C.) is also grateful to G. Pattenden, Nottingham University, U.K., for the accurate mass data of one of the compounds and to G. Mehta and A. Srikrishna, I.I.Sc, Bangalore, for spectral help and encouragement.