Total synthesis of dolabelide D.
The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.
Park
Peter K
PK
Department of Chemistry, Columbia University, New York, NY 10027, USA.
O'Malley
Steven J
SJ
Schmidt
Darby R
DR
Leighton
James L
JL
D000818:Animals; D004224:Diterpenes / Q000138:chemical synthesis*; D018942:Macrolides; D008974:Mollusca / Q000737:chemistry; D012821:Silanes / Q000737:chemistry
D004224:Diterpenes; D018942:Macrolides; D012821:Silanes; C509949:dolabelide D