Total synthesis of jerangolid A.
The first total synthesis of the antifungal polyketide jerangolid A has been accomplished. Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization for the construction of the dihydropyran subunit. The lactone segment was built through a tandem NaOMe conjugate addition-lactonization reaction, and further functionalized through a sequence consisting of iodination, I-Mg exchange, and hydroxymethylation. Other key steps in the synthesis featured a novel application of a phosphonamide-anion based olefination and a Julia-Kocienski reaction.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, QC H3C 3J7, Canada. stephen.hanessian@umontreal.ca
Focken
Thilo
T
Oza
Rupal
R
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D001688:Biological Products; D011714:Pyrans; C098368:jerangolid A