Carvone as a Versatile Chiral Building Block for Total Syntheses of Heterocyclic Sesquiterpenoids

Abstract

This review article is focused on the total syntheses of heterocyclic sesquiterpenoids starting from carvone since 1996.

Recent Advances of Total Syntheses of Diterpenoids Starting from Carvone

“…Among a variety of chiral pools such as -aminoacids [1], hydroxy acids [2], carbohydrates [3], quinic acid [4] and terpenoids [5], monoterpenoids have been used often due to easy availability of both enantiomers. Especially, both (R)-(-)-and (S)-(+)-carvones (1) as starting materials, in highly enantiomeric excess, are easily available at low cost, and have been employed for total syntheses of sesqui- [6], di-, and higher terpenoids [7] and alkaloids [8]. Their functional groups make a variety of stereoselective transformations of carvones (1) possible, such as acylation or alkylation at the  or -position, reductive alkylation at the -position, or conjugate addition at the -position of -unsaturated ketones.…”