89460-69-5

Upstream product

• 1629-58-9 4-penten-3-one 
• 5111-67-1 1-methyl-6-methoxy-2-tetralone 
• 1026044-47-2 2-[2-(2,6-Dimethyl-cyclohexa-1,5-dienyl)-ethyl]-4-methoxy-phenol 
• 167955-35-3 (4aS)-7-methoxy-1,4a-dimethyl-2,4a,9,10-tetrahydrophenanthrene 
• 167955-36-4 (4aS)-7-methoxy-1,4a-dimethyl-4,4a,9,10-tetrahydrophenanthrene 
• 167955-34-2 2-<2-(2,6-dimethyl-1,5-cyclohexadienyl)ethyl>-4-methoxyphenyl trifluoromethanesulfonate 
• 167955-33-1 1-(tert-butyldimethylsilyloxy)-2-<2-(2,6-dimethyl-1,5-cyclohexadienyl)ethyl>-4-methoxybenzene 
• 171924-31-5 2,6-dimethyl-1,5-cyclohexadienyl trifluoromethanesulfonate 
• 171924-19-9 2-tert-butyldimethylsilyloxy-5-methoxystyrene 
• 103261-31-0 2-hydroxy-5-methoxystyrene 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 167955-38-6 (4aR)-7-methoxy-1,4a-dimethyl-2-oxo-2,4a,9,10-tetrahydrophenanthrene 

Downstream Products

• 155028-15-2 (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one 
• 155039-11-5 (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene 
• 155028-09-4 (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene 
• 155028-17-4 (4R,5S,7R,8R,9R,10S,14R,16S)-20-<(Benzyloxy)methyl>-13-<(tert-butyldimethylsilyl)oxy>-16-ethoxy-21-norpicras-2,12-diene 
• 155028-21-0 (4R,5S,7R,8R,9R,10S,12R,13R,14R,16S)-13,20-Epoxy-16-ethoxy-12-(phenylseleno)-21-nitrilopicrasa-2-ene 
• 155028-16-3 (4R,5S,7R,8R,9R,10S,14R,16S)-20-<(Benzyloxy)methyl>-16-ethoxy-13-oxo-21-norpicras-2-ene 
• 155028-10-7 (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-<(tert-butyldimethylsilyl)oxy>-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one 
• 155028-11-8 (1R,4aS,4bR,8aS,9R,10aS)-8aβ-<(Benzyloxy)methyl>-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-9α-hydroxy-1α,4aβ-dimethylphenanthren-7-one 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis of a versatile intermediate for diterpene syntheses. Regioselective olefin insertion in asymmetric Heck reactions

We describe the details of the regioselective asymmetric cyclization of 5 to optically active 8 (95% ee), and the use of this tricyclic compound in the asymmetric synthesis of various diterpenes.

Synthesis of 15-Deoxy-16β-Ethoxybruceantin and Synthetic Efforts toward Bruceantin

Utilization of asymmetric Michael addition leads to chiral phenanthrenone (+)-4 suitable for the synthesis of Bruceantin.The D-ring is assembled by means of an intramolecular alkylation of the bromoacetals 25 while only the axial diastereomer 25ax proceeds smoothly.The formation of the cyanohydrin introduces the C-13 carboxyl group and tandem intramolecular alkylation provides the furan E-ring.The C-11,12 cis-diol 39 is readily transformed to the trans-diol 42 via an unusual Swern-type oxidation/reduction sequence.The C-2,3 olefin proves to be an efficient progenitor for the A-ring diosphenol function which can be introduced at the late stage of this synthesis. 15-Deoxy-16β-ethoxybruceantin 3 is accordingly prepared.Attempts to elaborate common intermediates toward the synthesis of bruceantin are described.The presence of an oxygen function at C-15 drastically changes the relative reactivity of the C-2,3 and C-11,12 olefinic bonds.

Asymmetric alkylation of α-aryl substituted carbonyl compounds by means of chiral phase transfer catalysts. Applications for the synthesis of (+)-podocarp-8(14)-en-13-one and of (-)-Wy-16,225, a potent analgesic agent

Asymmetric induction in the alkylation (alkyl halides and enones) of α-aryl substituted ketones, esters and lactones by means of CPTC has been evaluated. The catalysts used are the bromides of N-(p-trifluoromethyl) benzyl derivatives of cinchonine, cinchonidine, dihydrocinchonine and dihydrocinchonidine. The potential of the method is illustrated by the asymmetric synthesis of (+)-podocarp-8(14)-ene-13-one (13) and of (-)-Wy-16,225 (10), a bridged aminotetralin with potent analgesic properties.