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

Tetrahedron Letters

Enantiospecific total synthesis of pseudomonic acids from arabinose

GWJ Fleet, MJ Gough, TKM Shing

Index: Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Letters, 1983 , vol. 24, # 34 p. 3661 - 3664

Full Text: HTML

Citation Number: 22

Abstract

Pseudomonic acids A (I) and C (2) are members of a novel class of compounds with antibacterial and antimycoplasmal activity.' The first reported synthesis of racemic pseudomonic acid C involved a key step of coupling the racemic form of the pyranose aldehyde (3) with the ylid derived from the racemic form of the phosphonium salt (4)(Scheme 1). 2 Subsequent approaches to racemic3 pseudomonic acids have been directed ...

D-Ribose Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

1,5-Anhydro-D-arabinitol Structure

1,5-Anhydro-D-a...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

2-((2S,5R)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)-N,N-dimethylacetamide Structure

2-((2S,5R)-5-(2...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

ethyl (E)-4-((3a'S,4'S,7'S,7a'R)-7'-(2-((tert-butyldiphenylsilyl)oxy)ethyl)tetrahydro-4'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-4'-yl)-3-methylbut-2-enoate Structure

ethyl (E)-4-((3...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE Structure

5S-IODO-1S,6S-3...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

2-(R)-3,6-DIHYDRO-2H-PYRAN-3-YL-N,N-DIMETHYL-ACETAMIDE Structure

2-(R)-3,6-DIHYD...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enitol Structure

(E)-5,9-anhydro...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

1-((2S,5R)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)propan-2-one Structure

1-((2S,5R)-5-(2...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

1-((2S,3R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)propan-2-one Structure

1-((2S,3R,4R,5S...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

1-((3a'S,4'S,7'S,7a'R)-7'-(2-((tert-butyldiphenylsilyl)oxy)ethyl)tetrahydro-4'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-4'-yl)propan-2-one Structure

1-((3a'S,4'S,7'...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

INTEMEDIATE FOR MUPIRICIN Structure

INTEMEDIATE FOR...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enal Structure

(E)-5,9-anhydro...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

Ethyl monate C Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

Dimethylacetamide Dimethylacetal Structure

Dimethylacetami...

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

~82%

2-(R)-3,6-DIHYDRO-2H-PYRAN-3-YL-N,N-DIMETHYL-ACETAMIDE Structure

2-(R)-3,6-DIHYD...

D-Ribose Structure

~%

2-(R)-3,6-DIHYDRO-2H-PYRAN-3-YL-N,N-DIMETHYL-ACETAMIDE Structure

2-(R)-3,6-DIHYD...

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

tert-Butyl(chloro)diphenylsilane Structure

tert-Butyl(chlo...

~90%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

D-Ribose Structure

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

1,5-Anhydro-D-arabinitol Structure

1,5-Anhydro-D-a...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE Structure

5S-IODO-1S,6S-3...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

2-(R)-3,6-DIHYDRO-2H-PYRAN-3-YL-N,N-DIMETHYL-ACETAMIDE Structure

2-(R)-3,6-DIHYD...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL Structure

3-[2-(TERT-BUTY...

1,5-Anhydro-D-arabinitol Structure

1,5-Anhydro-D-a...

~%

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

D-Ribose Structure

~%

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE Structure

5S-IODO-1S,6S-3...

~87%

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

D-Ribose Structure

~%

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

METHYL4-NITROBENZENESULFONATE Structure

METHYL4-NITROBE...

~%

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

2-(R)-3,6-DIHYDRO-2H-PYRAN-3-YL-N,N-DIMETHYL-ACETAMIDE Structure

2-(R)-3,6-DIHYD...

~%

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

1,5-Anhydro-D-arabinitol Structure

1,5-Anhydro-D-a...

~%

(3S,4R)-3-METHYL-4-N-PHENYLAMINO-PIPERIDINE Structure

(3S,4R)-3-METHY...

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]