José López

Microbiological hydroxylation in the drimane series

Abstract The Products of the microbiological hydroxylation of drimenol and related compounds by Mucor plumbeus and Rhizopus arrhizus were investigated Complementary results (hydroxylation at 3β- and/or 6α-positions) were obtained with both microorganism.

(−)-3β-Acetoxydrimenin from the leaves of Drimys winteri

Abstract A new natural product, 3β-acetoxydrimenin was isolated from the petrol extract of the leaves of Drimys winteri which also contains the known compounds safrol, drimenol and polygodial. The structure of the new compound was determined by chemical and spectroscopic methods.

An Alternative Partial Synthesis of (-)-Polygodial

Abstract A four steps partial synthesis of (-)-polygodial (1) has been achieved, using (-)-drimenol (2) as starting material.

A novel xanthone as secondary metabolite fromCentaurium cachanlahuen

From the plantCentaurium cachanlahuen, swertiaperenine1, swercherine2, decusatine4, oleanolic acid5 and the xanthone 1,8-dihydroxy-2,3,4,6-tetramethoxy-9H-xanthone3 were isolated and characterized.

Synthesis of 1.3 Dioxans Related with Ambergris

Abstract An improved preparation of the odoriferous acetal (4aR, 6aS, 10aS, 10bR)-4a,7,7,10a-tetramethylper-hydronaphtho[2, 1-d] [1, 3] dioxin (4) and related products are described. The synthesis of 4 is accomplished in six steps, starting with the readily available sesquiterpene (-)-drimenol (5) (overall yield 19.1%).

Synthesis of (-)-12-Nor-Drim-9(11)-En-8-One a Versatile Synthon for the Preparation of Natural Terpenoids

Abstract A short synthesis of the optically active enone 1 from (-) polygodial is described.

Formal Synthesis of Ambrox® and 9-Epiambrox

Abstract (-)-Drimenol (5) was used as starting material for the synthesis of diastereoisomeric diols 3 and 4, through the nitrile 7, Compounds 3 and 4 are the direct precursors of Ambrox® (1) and 9-epiambrox (2).

A Synthetic Approach to Ring B of Forskolin

Abstract A model bicyclic diol (3) incorporating the complete array of oxygenated function of the B ring portion of forskolin (1) has been synthetized using (-)drimenol (2) as starting material.

Functionalization of natural drimanic compounds via microbial/chemical tandem reactions

Abstract The direct microbial 3β-hydroxylation of drimanic terpenes by filamentous fungi, followed by a transfer of the functionalization from the 3β- to the 1α-position has been used for preparing derivatives of antifeedant terpenic compounds bearing an additional 1α-hydroxyl group. The semisynthesis of 1α-hydroxypolygodial is described as an example.

A Revision of the Absolute Configuration of Drim-9(11)-en-8α-ol

Abstract A new synthesis of the drimane sesquiterpene 1has been performed using (-)drimenol (3)as chiral starting material. Comparison of the specific rotation of the natural and synthetic 1established the absolute configuration of the naturally occurring 1as the normal drimane skeleton.