79691-11-5

Upstream product

• 27763-54-8 (S)-2-methylbutanoyl chloride 
• 79902-31-1 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 96011-27-7 (S)-2-Methyl-butyric acid (1S,3R,4S,4aR,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-hydroxy-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester 
• 75330-75-5 lovastatin 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 118682-50-1 (S)-2-Methyl-butyric acid (1S,3R,5S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-5-hydroxy-3,7-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-24-4 (S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-trifluoromethanesulfonyloxy-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 85614-12-6 (S)-2-Methyl-butyric acid (1S,3S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-18-6 (S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-17-5 2-methyl-butyric acid 8-{2-[4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-6-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 153079-20-0 (S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-hydroxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-22-2 (S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-21-1 (S)-2-Methyl-butyric acid (1S,4S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-7-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 153079-19-7 (S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-formyloxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 

Downstream Products

• 83268-65-9 6(R)-<2-<8(S)-(benzyloxy)-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 83268-64-8 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-(benzyloxy)-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-hydroxy-3,4,5,6-tetrahydro-2H-pyran 
• 83268-63-7 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-(benzyloxy)-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran 
• 103063-54-3 6(S)-<2-<8(S)-<<2(S)-methylbutanoyl>oxy>-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl>ethyl>-4-(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 105227-51-8 lovastatin 
• 105227-52-9 (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 102963-74-6 N-benzyl 7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R)-<(tert-butyldimethylsilyl)oxy>-5(R)-hydroxyheptanoic acid amide 
• 75330-75-5 lovastatin 

Relevant academic research and scientific papers

Stereocontrolled functionalization of the diene system of compactin

A facile regio- and stereo selective γ-functionlization of the 1,3-diene system of compactin via the key dienone 3 is described.

OXO-ANALOGS OF MEVINOLIN-LIKE ANTIHYPER-CHOLESTEROLEMIC AGENTS

Mevinolin-like compounds in which the lactone is opened and the hydroxyl function produced thereby is replaced by an oxo function are potent HMG-CoA reductase inhibitors possessing one less asymmetric center

Remote Diastereoselection in the Asymmetric Total Synthesis of Mevinolin

The asymmetric total synthesis of mevinolin (1a) is described.The key diastereoselective processes used to parlay the lone stereogenic center of asymmetrically produced (S)-pulegone (2a) to mevinolin include orthoester-Claisen rearrangement of 2d to 3a, stereoselective iodolactonization of 3e to 4, Eschenmoser-Claisen rearrangement of 6 to 7a, stereoselective intramolecular ene reaction of 7b to 8, and a highly diastereoselective cyclocondesation of aldehyde 10 with Danishefsky's diene.The cyclocondensation reaction was found to be quite sensitive to the reactionconditions in which the use of TiCl4 produced a 90:10 mixture of 11/12 while MgBr2 gave a 22:78 mixture

3-Hydroxy-3-methylglutaryl-coenzyme A Reductase Inhibitors. 4. Side Chain Ester Derivatives of Mevinolin

Modification of the 2(S)-methylbutyryl moiety of mevinolin led to a series of side chain ester derivatives.A systematic exploration of the structure-activity relationships showed that the introduction of an additional aliphatic group on the carbon α to the carbonyl group increased potency.This obsrevation led to the synthesis of compound 16, which has about 2.5 times the intrinsic inhibitory activity of mevinolin.

Reductive Transformation and Cyclopropanation of Mevinolin (α-Methylcompactin). Generation of Chirality in the 1,4-Hydrostannation of a Cyclic Diene

Conversion of mevinolin by direct reductive procedures as well as by indirect chemical transformations has permitted the preparation of the various di- and tetrahydro derivatives.Cyclopropanation of mevinolin and its derivatives has furnished mono- and di

Structural Modification of Mevinolin

Synthetic strategies are described for modifying the side-chain ester and lactone moieties of mevinolin (1), a potent, competitive HMG-CoA reductase inhibitor isolated from cultures of Aspergillus terreus.A general route for preparing side-chain ether analogues of 1 is disclosed.Central to the success of this multistep route is the use of a method for reversibly masking the lactone moiety as a hemiacetal ether.The merit of this strategy is demonstrated again in the route developed for elaborating mevalonate analogue 11 from 1.Finally, a new, versatile, and efficientmethod is presented for homologating five- and six-membered lactones and is used to prepare carboxylate 27, a homologue of 1.