Total synthesis of (+/-)-kellermanoldione: stepwise cycloaddition of a functionalized diene and allenoate.
The total synthesis of the diterpene kellermanoldione 1 is reported. Stepwise [4 + 2] cycloaddition of the ketal diene 8 and the allenoate 3 afforded the exo adduct 10x as the major product. It was converted into 1 via six steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Cordova
Jesus
J
Murakami
Masayuki
M
D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism
D004224:Diterpenes; D011090:Polyenes; C543449:kellermanoldione