Total synthesis of (+/-)-hedychilactone B: stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems.
[reaction: see text] The total synthesis of the diterpene hedychilactone B 1 is reported. The exo adduct 4x, the major product of the stepwise [4+2] cycloaddition of the diene 2 and the allenoate 3, has been converted into 1 via 7 steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether and an E-selective olefination.
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
Murakami
Masayuki
M
D000466:Alkadienes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006868:Hydrolysis; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D009281:Naphthalenes / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000475:Alkenes; D000893:Anti-Inflammatory Agents; D004224:Diterpenes; D004987:Ethers; D007783:Lactones; D009281:Naphthalenes; D012821:Silanes; D012997:Solvents; C518569:hedychilactone B; C007229:decalin