Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B.
Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.
Boukouvalas
John
J
Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
Wang
Jian-Xin
JX
Marion
Olivier
O
Ndzi
Bruno
B
D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D030521:Zingiberaceae / Q000737:chemistry
D000447:Aldehydes; D000970:Antineoplastic Agents; D004224:Diterpenes; D007783:Lactones; D013729:Terpenes; C520384:zerumin B