Total synthesis of jerangolid A.
Org Lett
; 12(14): 3172-5, 2010 Jul 16.
Article
em En
| MEDLINE
| ID: mdl-20565089
ABSTRACT
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.
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Base de dados:
MEDLINE
Assunto principal:
Antifúngicos
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article