851279-15-7

Upstream product

• 189082-97-1 3,4-bis(benzyloxy)phenyl formate 
• 189082-99-3 3,4-di-O-benzyl-2-bromo-1-O-tert-butyldimethylsilylbenzenetriol 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 316803-64-2 Acetic acid (1R,2R,4aS,8aS)-1-iodomethyl-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester 
• 86546-84-1 (5S,8R,10S)-drim-9⁽¹¹⁾-en-8-ol 
• 468-68-8 (-)-drimenol 
• 52617-99-9 (+)-drimane-8,11-diol 
• 851279-13-5 1,2-di-O-benzyl-4-O-diethylcarbamoylbenzenetriol 
• 851279-14-6 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol 
• 105426-71-9 (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde 
• 247577-70-4 Acetic acid (R)-[4,5-bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-methyl ester 

Downstream Products

• 257288-33-8 8-epi-19,20-di-O-benzyl-puupehenol 
• 851279-17-9 19,20-di-O-benzyl-puupehenol-6-ene 

Relevant academic research and scientific papers

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

(Chemical Equation Presented) 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-cyanopuupehenone, were accomplished.

Enantiospecific synthesis of (+)-puupehenone from (-)-sclareol and protocatechualdehyde

The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni.