Total synthesis of (+/-)-kalihinol C.
The total synthesis of kalihinol C, a bis-isonitrile marine diterpenoid isolated from Acanthella sp., is reported. The decalin framework was established via an intramolecular Diels-Alder cycloaddition and subsequently functionalized through a series of substrate-controlled diastereoselective transformations to install the tertiary isonitrile, beta-hydroxy isonitrile, and pendant tetrahydrofuranyl ring.
White
Ryan D
RD
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Keaney
Gregg F
GF
Slown
Corin D
CD
Wood
John L
JL
D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry
D000962:Antimalarials; D004224:Diterpenes; D009570:Nitriles; C431469:kalihinane; C484758:kalihinol C