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

Total synthesis of the hypocholesterolemic agent compactin

CT Hsu, NY Wang, LH Latimer…

Index: Journal of the American Chemical Society, , vol. 105, # 3 p. 593 - 601

Full Text: HTML

Citation Number: 37

Abstract

... 0002-7863/83/1505-0593%01.50/0 I , , 0 1983 American Chemical Society ... This unexpected turn of events forced us to the utilization of a less convergent approach for the ... Chemical shifts are reported in 6 (peak multiplicity, coupling constant if appropriate, number of protons). ...

(S)-2-methylbutyric acid Structure

(S)-2-methylbut...

~97%

(S)-(+)-2-HEPTANOL Structure

(S)-(+)-2-HEPTANOL

1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene Structure

1β,4α-bis(benzy...

~%

Mevastatin Structure

1β,4α-bis(benzyloxy)-7-oxo-1,2,3,4,4aβ,7,8,8aα-octahydronaphthalene Structure

1β,4α-bis(benzy...

~%

Mevastatin Structure

(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione Structure

(+/-)-1,4,5,8,9...

~%

Mevastatin Structure

(1S,4S,4aR,8aR)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1,4-diol Structure

(1S,4S,4aR,8aR)...

~%

Mevastatin Structure

(4aS,5R,8R,8aS)-5,8-bis(benzyloxy)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-ol Structure

(4aS,5R,8R,8aS)...

~%

Mevastatin Structure

1β,4α-bis(benzyloxy)-7α-hydroxy-6β-(phenylselenyl)-4aβ,8aα-decahydronaphthalene Structure

1β,4α-bis(benzy...

~%

Mevastatin Structure

N/A Structure

~%

Mevastatin Structure

7α-acetoxy-1β,4α-bis(benzyloxy)-6β-(phenylselenyl)-4aβ,8aα-decahydronaphthalene Structure

7α-acetoxy-1β,4...

~%

Mevastatin Structure

(4aα,8aβ)-5β,8α-bis(benzyloxy)-2-methylene-3-oxo-1β-[3-(1-ethoxyethoxy)propyl]decahydronaphthalene Structure

(4aα,8aβ)-5β,8α...

~%

Mevastatin Structure

(4aα,8aβ)-5β,8α-bis(benzyloxy)-2(hydroxymethyl)-3-oxo-1β-[3-(1-ethoxyethoxy)propyl]decahydronaphthalene Structure

(4aα,8aβ)-5β,8α...

~%

Mevastatin Structure

((1R,4aR,5S,8S,8aR)-5,8-bis(benzyloxy)-1-(3-(1-ethoxyethoxy)propyl)-3-oxodecahydronaphthalen-2-yl)methyl methanesulfonate Structure

((1R,4aR,5S,8S,...

~%

Mevastatin Structure

methyl 3,5-dihydroxy-7-[2-methyl-8-(2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoate Structure

methyl 3,5-dihy...

~%

Mevastatin Structure

3,5-bis-epi-compactin Structure

3,5-bis-epi-com...

(S)-2-methylbutyric acid Structure

(S)-2-methylbut...

~%

Mevastatin Structure

5β,8α-dihydroxy-2β-methyl-1β-[3-(1-ethoxyethoxy)propyl]-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene Structure

5β,8α-dihydroxy...

~%

Mevastatin Structure

5β,8α-dibenzyloxy-2β-methyl-1β-[3-(1-ethoxyethoxy)propyl]-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene Structure

5β,8α-dibenzylo...

~%

Mevastatin Structure

N/A Structure

~%

Mevastatin Structure

(S)-(+)-2-HEPTANOL Structure

(S)-(+)-2-HEPTANOL

~%

Mevastatin Structure

8α-[(S)-(2-methylbutyryl)oxy]-2β-methyl-1β-(3-hydroxypropyl)-1,2,6,7,8,8aβ-hexahydronaphthalene Structure

8α-[(S)-(2-meth...

~%

Mevastatin Structure

N/A Structure

~%

Mevastatin Structure

8α-[(S)-(2-methylbutyryl)oxy]-2β-methyl-1β-[3-(1-ethoxyethoxy)propyl]-1,2,6,7,8,8aβ-hexahydronaphthalene Structure

8α-[(S)-(2-meth...

~%

Mevastatin Structure

(1S,4S,4aR,7S,8S,8aR)-8-(3-(1-ethoxyethoxy)propyl)-4-hydroxy-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate Structure

(1S,4S,4aR,7S,8...

~%

Mevastatin Structure

methyl 5-hydroxy-7-((1S,2S,8S,8aR)-2-methyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3-oxoheptanoate Structure

methyl 5-hydrox...

~%

Mevastatin Structure

(1S,4S,7S,8S,8aR)-8-(3-(1-ethoxyethoxy)propyl)-7-methyl-4-((methylsulfonyl)oxy)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate Structure

(1S,4S,7S,8S,8a...

~%

Mevastatin Structure

(1S,4S,4aR,5S,6S,8aR)-5-(3-(1-ethoxyethoxy)propyl)-6-methyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene-1,4-diyl (2S,2'S)-bis(2-methylbutanoate) Structure

(1S,4S,4aR,5S,6...

~%

Mevastatin Structure