199438-60-3

Upstream product

• 68985-10-4 (4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde 
• 189082-97-1 3,4-bis(benzyloxy)phenyl formate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 1616-86-0 cis-abienol 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 165816-95-5 8α-acetoxydriman-11-al 
• 199438-57-8 8S-13,14,15,16-tetranorlabdan-12-al 
• 88755-15-1 1,2-dibenzyloxy-4-methoxybenzene 
• 199438-59-0 8S-1,2-di-O-benzyl-3-(11'-hydroxydriman-11'-yl)-4-O-methylbenzenetriol 
• 199438-58-9 8S-labda-12Z,13-diene 
• 208102-92-5 tert-Butyl-dimethyl-[(E)-2-((1R,2S,4aS,8aR)-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-vinyloxy]-silane 
• 199438-55-6 (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of wiendendiol-A and wiedendiol-B from Labdane diterpenes

Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)- sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 85.95- driman-11-al (26), by two alternative routes starting from 7 and (+)-cis- abienol (8) is also described. 21 prepared from protocatchhualdehyde (17) was used as somatic synthon for preparing 1 and 2.

Enantiospecific synthesis of wiedendiol-B from (-)-sclareol and (+) cis-abienol

The first enantiospecific synthesis of the cholesteryl ester transfer protein (CETP) inhibitor wiedendiol-B (1) is described. The drimanic synthon was prepared from (-)-sclareol (4) and (+)-cis-abienol (13) by two alternative routes. The key steps of the reaction sequences are the chemo- and diastereoselective hydrogenation of the C8-C9 double bond of enal 6 and the stereoselective cationic hydrogenation of the hydroxyl group of 13, respectively, and the selective reduction of benzyl groups of 15.