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.
Armstrong
Veronica
V
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Correo 22, Santiago, Chile. aarmstrl@puc.cl
Barrero
Alejandro F
AF
Alvarez-Manzaneda
Enrique J
EJ
Cortés
Manuel
M
Sepúlveda
Beatriz
B
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