Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (-)-sclareol

A F Barrero; M Cortés; E A Manzaneda; E Cabrera; R Chahboun; M Lara; A R Rivas

doi:10.1021/np990140q

Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (-)-sclareol

J Nat Prod. 1999 Nov;62(11):1488-91. doi: 10.1021/np990140q.

Authors

A F Barrero¹, M Cortés, E A Manzaneda, E Cabrera, R Chahboun, M Lara, A R Rivas

Affiliation

¹ Departamento de Química Orgánica, Instituto de Biotecnología, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071-Granada, Spain. afbarre@goliat.ugr.es

PMID: 10579858
DOI: 10.1021/np990140q

Abstract

The first syntheses are reported for recently isolated drimanes 11, 12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Benzofurans / chemical synthesis*
Benzofurans / pharmacology
Diterpenes / chemistry*
Drug Screening Assays, Antitumor
Humans
Leukemia P388 / drug therapy
Naphthalenes / chemical synthesis*
Naphthalenes / pharmacology
Porifera / chemistry*
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / pharmacology
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

11,12-diacetoxydrimane
11,12-epoxydrim-8,12-en-11-ol
Antineoplastic Agents
Benzofurans
Diterpenes
Naphthalenes
Sesquiterpenes
warburganal
sclareol