The total synthesis of (+/-)-merrilactone A.
The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Dielsminus signAlder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 right arrow 1).
Birman
Vladimir B
VB
Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
Danishefsky
Samuel J
SJ
D029523:Illicium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007783:Lactones; D012717:Sesquiterpenes; C458341:merrilactone A