An efficient stereoselective synthesis of cytotoxic 8-epipuupehedione.
An efficient and highly stereoselective synthesis of cytotoxic 8-epipuupehedione (1b) was achieved starting from natural (-)-drimenol (6). The key step to obtain stereoselectivity was the simultaneous demethylation and oxidation of the dihydrobenzopyran methoxy derivatives 10a and 10b.
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Correo 22, Santiago, Chile. aarmstrl@puc.cl
Veronica
V
Armstrong
Alejandro F
AF
Barrero
Enrique J
EJ
Alvarez-Manzaneda
Manuel
M
Cortés
Beatriz
B
Sepúlveda
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000081223:Polycyclic Sesquiterpenes; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C481243:8-epipuupehedione; D000970:Antineoplastic Agents; D000081223:Polycyclic Sesquiterpenes; D013729:Terpenes; C481244:drimenol