Two cytotoxic terpenes, alpha-santonin (1) and sclareol (3) were biotransformed by a plant pathogenic fungus Botrytis cinerea to produce oxidized metabolites in high yields. Alpha-Santonin (1) on fermentation with the fungus for ten days afforded a hydroxylated metabolite identified as 11beta-hydroxy-alpha-santonin (2) in a high yield (83%), while sclareol (3) was metabolized to epoxysclareol (...

Hyphozyma roseoniger is a filamentous yeast used for its biocatalytic ability to convert sclareol, plant diterpenoid ambradiol, an intermediate ambrafuran, which sought-after fixative in the perfume industry. Metabolite profiling suitable investigative tool dissect biochemical steps involved reaction by H. from sclareol ambradiol. suspensions were grown batch culture simulate growth bioreactor ...

The first enantiospecific synthesis of akaol A, a marine sesquiterpene quinol, has been achieved. Key steps of the synthetic sequence are the oxidative degradation of (-)-sclareol to a dinorlabdane ketoester, mediated by the ozone-lead(IV) acetate system, the diastereoselective α-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels-Alder cycloadd...

Flavonoids are polyphenolic plant secondary metabolites with many purposes, including providing pigmentation in plants and anti-oxidant and anti-cancerous activities in humans. There are over 10,000 different flavonoids known, making them one of the largest groups of natural products. One major sub-class of flavonoids is the flavan-3-ols, which are known for their health benefits and the abilit...

[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...

The first synthesis of Luffarin I, sesterterpenolide isolated from sponge Luffariella geometrica, has been accomplished from commercially available sclareol. The key strategy involved in this synthesis is the diastereoselective reduction of an intermediate ketone. Luffarin I against human solid tumor cell lines showed antiproliferative activities (GI50) in the range 12-17 μM.

The first syntheses are reported for recently isolated drimanes 11, 12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.

Trinorlabdane 1,5-diketones (7, 10a,b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerio...