e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy.

T Hiyama, T Minami, K Takahashi

Index: Bulletin of the Chemical Society of Japan, , vol. 68, # 1 p. 364 - 372

Full Text: HTML

Citation Number: 37

Abstract

... by asymmetric reduction of /?,£-diketo esters derived from the Taber's alcohol or L-tartrate followed by a series of chemical transformations, and ... Jpn., 68, No. 1 (1995) Artificial HMG-CoA Reductase Inhibitor NK-104 Table 1. Olefination of (±)-4a with reagent 3b Preparation of 3b ...

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...

~81%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

N/A Structure

~%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate Structure

isopropyl (2S,3...

~%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate Structure

isopropyl (2S,3...

~%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate Structure

isopropyl (2S,3...

~%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

N/A Structure

~%

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Structure

(4R-Cis)-6-Hydr...

2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol Structure

2-Cyclopropyl-4...

~%

2-Cyclopropyl-3-[(diphenylphosphinyl)methyl]-4-(4-fluorophenyl)quinoline Structure

2-Cyclopropyl-3...

2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol Structure

2-Cyclopropyl-4...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline Structure

3-(Bromomethyl)...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

N/A Structure

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate Structure

isopropyl (2S,3...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate Structure

isopropyl (2S,3...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate Structure

isopropyl (2S,3...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

N/A Structure

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...

2-Cyclopropyl-3-[(diphenylphosphinyl)methyl]-4-(4-fluorophenyl)quinoline Structure

2-Cyclopropyl-3...

~%

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Structure

(4R,6S)-6-[(1E)...

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate Structure

isopropyl (2S,3...

~%

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate Structure

isopropyl (2S,3...

~%

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...

isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate Structure

isopropyl (2S,3...

~%

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...

N/A Structure

~%

tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate Structure

tert-Butyl (4R-...