First enantiospecific synthesis of marine sesquiterpene quinol akaol A.

A new Enantiospecific Route toward Monocarbocyclic Terpenoids: Synthesis of (-)- Caparrapi Oxide

A new and efficient strategy is described for carrying out the enantiospecific synthesis of monocarbocyclic terpenoids from (-)-sclareol (1). The key steps are the Grob scission of l l p toluenesulphonyloxydriman-7ct-ol (2) to give the tobacco seco-sesquiterpene 3 and the Baeyer-Villiger oxidation of 4-[(1'S, 2'S)-2'-formyl-2',6',6'-trimethylcyclohexyl]-2-butanone (4), derived from 3. The first...

First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.

[reaction: see text] A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyan...

Enantiospecific first total synthesis of cucumin-H

Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products.

Marine red algae (Rhodophyta) are a rich source of bioactive halogenated natural products. The biogenesis of the cyclic halogenated terpene marine natural products, in particular, has attracted sustained interest in part because terpenes are the biogenic precursors of many bioactive metabolites. The first enzymatic asymmetric bromination and cyclization of a terpene, producing marine natural pr...

Biotransformation of the marine sesquiterpene pacifenol by a facultative marine fungus.

Continued investigation of the marine alga Laurencia claviformis has led to the isolation of pacifenol, a halogenated sesquiterpene as the major metabolite. The microbial transformation of pacifenol is reported. It was cultivated with a marine strain of Penicillium brevicompactum yielding a new compound. The structure was elucidated on the basis of spectroscopic data. The anti-microbial activit...