123049-73-0

Upstream product

• 158041-69-1 (3R,4aR,7S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 158041-68-0 (3R,4aR,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 158041-67-9 (2Z,8E,10E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-one 
• 158041-79-3 (E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-7-[(1S,2S,6S,8S,8aR)-2,6-dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-5-oxo-hept-6-enoic acid methyl ester 
• 158111-07-0 (R)-7-[(1S,2S,6S,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3-hydroxy-5-oxo-heptanoic acid methyl ester 
• 158041-77-1 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 147328-70-9 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-formyl-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 158041-78-2 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-hydroxymethyl-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 158041-76-0 (1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol 
• 158041-70-4 (1S,3R,4aR,7S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol 
• 158111-08-1 (3R,5R)-7-[(1S,2S,6S,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels - Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]6-methyl-2,8,10-dodecatrien-4-one

3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels - Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of (E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of (R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (4-)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.