200420-37-7Relevant academic research and scientific papers
Total synthesis of (-)-verrucarol, a component of naturally occurring verrucarin A
Ishihara, Jun,Nonaka, Rie,Terasawa, Yuki,Shiraki, Ryota,Yabu, Kazuo,Kataoka, Hiromi,Ochiai, Yuichi,Tadano, Kin-Ichi
, p. 8311 - 8314 (1997)
Total synthesis of (-)-verrucarol (1) was achieved starting from D- glucose-derived bicyclic lactone 4 through 1) a stereoselective asymmetric quaternization of the α-carbon of the lactone, 2) Diechmann cyclization for access to the C-ring equivalent, 3) a skeletal rearrangement for the trichothecene ring system, and 4) the final stereoselective epoxidation of an exo-methylene group.
Total synthesis of (-)-verrucarol
Ishihara, Jun,Nonaka, Rie,Terasawa, Yuki,Shiraki, Ryota,Yabu, Kazuo,Kataoka, Hiromi,Ochiai, Yuichi,Tadano, Kin-Ichi
, p. 2679 - 2688 (2007/10/03)
We have achieved the total synthesis of (-)-verrucarol, a trichothecene sesquiterpenoid obtained as a hydrolysis product of the naturally occurring verrucarin A. Our total synthesis began with the previously reported enantiometrically pure bicyclic α-methylated γ-lactone, which was prepared from D-glucose. The key steps for the total synthesis were (1) aldol-like carbon-carbon bond formation applied to the starting lactone using a four- carbon aldehyde as an electrophile for introduction of the quaternary stereogenic carbon sharing the B and C-rings of the trichothecene skeleton, (2) Dieckmann cyclization of the derived ε-ester lactone for construction of the C-ring equivalent, (3) Barton's decarboxylative oxygenation for conversion of a carboxylic acid functionality in the Dieckmann cyclization product into a hydroxyl group, (4) skeletal enlargement strategy for the crucial trichothecene skeleton construction, and (5) the final stereoselective formation of the exo-epoxy ring at the methylene carbon in the bridge constituting the B and C-rings.
