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

Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (π-allyl) tricarbonyliron lactone complex

RW Bates, E Fernández-Megía, SV Ley…

Index: Bates, Roderick W.; Fernandez-Megia, Eduardo; Ley, Steven V.; Ruck-Braun, Karola; Matthew Tilbrook Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 14 p. 1917 - 1925

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Citation Number: 2

Abstract

Page 1. J. Chem. Soc., Perkin Trans. 1, 1999, 1917–1925 1917 Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (π-allyl)tricarbonyliron lactone complex Roderick W. Bates,b Eduardo Fernández-Megía,a Steven V. Ley,*a Karola Rück-Brauna and D. Matthew G. Tilbrookab ... The resulting mixture was diluted with Et2O (70 cm3) and washed with H2O (3 × 50 cm3) and brine. ...

Diphenylmethyl [2E,4E,7R,(2'R,3'R)]-11-(3'-hydroxymethyl-4'-oxooxetan-2'-yl)-3,5,7-trimethylundeca-2,4-dienoate Structure

Diphenylmethyl ...

~76%

hymeglusin Structure

(2Z,8R)-8-Methylundec-2-en-10-yn-1-ol Structure

(2Z,8R)-8-Methy...

~%

hymeglusin Structure

(6R)-6-Methyl-7-(tetrahydro-2H-pyran-2-yloxy)heptanal Structure

(6R)-6-Methyl-7...

~%

hymeglusin Structure

(2Z,8R,10E)-8,10-Dimethyl-11-iodoundeca-2,10-dien-1-ol Structure

(2Z,8R,10E)-8,1...

~%

hymeglusin Structure

(7R)-7-Methyl-8-(tetrahydro-2H-pyran-2-yloxy)oct-1-ene Structure

(7R)-7-Methyl-8...

~%

hymeglusin Structure

(2Z,8R)-8-Methyl-9-(tetrahydro-2H-pyran-2-yloxy)non-2-en-1-ol Structure

(2Z,8R)-8-Methy...

~%

hymeglusin Structure

Methyl (2Z,8R)-8-methyl-9-(tetrahydro-2H-pyran-2-yloxy)-non-2-enoate Structure

Methyl (2Z,8R)-...

~%

hymeglusin Structure

(2R,7Z)-9-(tert-Butyldiphenylsilyloxy)-2-methylnon-7-en-1-ol Structure

(2R,7Z)-9-(tert...

~%

hymeglusin Structure

(2Z,8R)-1-(tert-Butyldiphenylsilyloxy)-8-methylundec-2-en-10-yne Structure

(2Z,8R)-1-(tert...

~%

hymeglusin Structure

(2Z,8R)-1-(tert-Butyldiphenylsilyloxy)-8-methyl-9-(tetrahydro-2H-pyran-2-yloxy)non-2-ene Structure

(2Z,8R)-1-(tert...

~%

hymeglusin Structure

(2R,7Z)-9-(tert-Butyldiphenylsilyloxy)-2-methyl-1-(p-tolylsulfonyloxy)non-7-ene Structure

(2R,7Z)-9-(tert...

~%

hymeglusin Structure

Diphenylmethyl (2E,4E,7R,12Z)-14-hydroxy-3,5,7-trimethyltetradeca-2,4,12-trienoate Structure

Diphenylmethyl ...

~%

hymeglusin Structure

Diphenylmethyl (2E,4E,7R,12R,13R)-12,13-epoxy-14-oxo-3,5,7-trimethyltetradeca-2,4-dienoate Structure

Diphenylmethyl ...

~%

hymeglusin Structure

Diphenylmethyl (2E,4E,7R,12R,13S)-12,13-epoxy-3,5,7-trimethylpentadeca-2,4,14-trienoate Structure

Diphenylmethyl ...

~%

hymeglusin Structure

Diphenylmethyl [2E,4R/S,5S/R,7R,(2'R,3'R)]-4,5-epoxy-11-(4'-oxo-3'-vinyloxetan-2'-yl)-3,5,7-trimethylundec-2-enoate Structure

Diphenylmethyl ...

~%

hymeglusin Structure

Diphenylmethyl [2E,4R/S,5S/R,7R,(2'R,3'R)]-4,5-epoxy-11-(3'-hydroxymethyl-4'-oxooxetan-2'-yl)-3,5,7-trimethylundec-2-enoate Structure

Diphenylmethyl ...

~%

hymeglusin Structure

N/A Structure

~%

hymeglusin Structure

Total synthesis of L-659,699, a novel inhibitor of cholester...

[Chiang; Yang; Heck; Chabala; Chang Journal of Organic Chemistry, 1989 , vol. 54, # 24 p. 5708 - 5712]

Total synthesis of 1233A

[Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 832 - 839]

Total synthesis of 1233A

[Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 832 - 839]

Total synthesis of 1233A

[Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 832 - 839]

Total synthesis of 1233A

[Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 832 - 839]