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Stereoselective Synthesis of 8,12-Furanoeudesmanes From Santonin. Absolute Stereochemistry of Natural Furanoeudesma-1,3-diene and Tubipofurane

Stereoselective Synthesis of 8,12-Furanoeudesmanes From Santonin. Absolute Stereochemistry of Natural Furanoeudesma-1,3-diene and Tubipofurane

Gonzalo Blay, Luz Cardona, Begoña García, José R. Pedro, Juan J. Sánchez

J Org Chem. 1996 May 31;61(11):3815-3819.

PMID: 11667234

Abstract:

Ketobutenolide 3, easily obtained from santonin (1), has been transformed into two natural furanoeudesmanes 4 and 5, isolated from Commiphora molmol and Tubipora musica, respectively. trans- And cis-decalin systems were obtained by stereoselective reduction of the C(4)-C(5) double bond in 3 in the following way: hydrogenation of 3 over Pd/C followed by acidic treatment gave the cis isomer 10 as the major product; selective hydrogenation of the C(1)-C(2) double bond with the Wilkinson's catalyst followed by reduction with NaTeH yielded mainly the trans isomer 9. Compounds 9 and 10 were transformed into 4 and 5 in parallel sequences. Optical rotation and CD measurements of the synthetic products revealed that the stereochemistry of both natural products should be revised to their enantiomeric form.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP87605934	Furanoeudesma 1,3-diene		87605-93-4	Price

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