Approach to the synthesis of antitumor quassinoids from labdane diterpenes: an efficient synthesis of a picrasane-related intermediate

A F Barrero; E J Alvarez-Manzaneda; R Alvarez-Manzaneda; R Chahboun; R Meneses; J M Cuerva; M Aparicio; J L Romera

doi:10.1021/ol0065322

Approach to the synthesis of antitumor quassinoids from labdane diterpenes: an efficient synthesis of a picrasane-related intermediate

Org Lett. 2001 Mar 8;3(5):647-50. doi: 10.1021/ol0065322.

Authors

A F Barrero¹, E J Alvarez-Manzaneda, R Alvarez-Manzaneda, R Chahboun, R Meneses, J M Cuerva, M Aparicio, J L Romera

Affiliation

¹ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain. afbarre@goliat.ugr.es

PMID: 11259027
DOI: 10.1021/ol0065322

Abstract

[structure: see text]. The tetracyclic ketal 24, a suitable intermediate for the synthesis of antitumor pentacyclic quassinoids, has been efficiently prepared from communic acids (5a-c), via methyl ketone 9. The synthetic sequence from 9 to 24 consists of 15 steps in 12% overall yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Diterpenes / chemical synthesis*
Plants, Medicinal / chemistry
Quassins*
Terpenes

Substances

Antineoplastic Agents, Phytogenic
Diterpenes
Quassins
Terpenes
picrasane