Total synthesis and immunosuppressive activity of (-)-pateamine A and related compounds: Implementation of a β-lactam-based macrocyclization

…, HA Shea, K Park, JM Langenhan, L Sun…

Index: Romo, Daniel; Rzasa, Robert M.; Shea, Helene A.; Park, Kaapjoo; Langenhan, Joseph M.; Sun, Luo; Akhiezer, Alexander; Liu, Jun O. Journal of the American Chemical Society, 1998 , vol. 120, # 47 p. 12237 - 12254

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Citation Number: 130

Abstract

The asymmetric synthesis of the potent immunosuppressive agent (-)-pateamine A isolated from the marine sponge Mycale sp. is described. A key strategy employed in the synthesis was a β-lactam-based macrocyclization to form the 19-membered dilactone macrolide. The synthesis confirms the relative and absolute stereochemistry as 3 R, 5 S, 10 S, 24 S and sets the stage for studies into the mechanism of action of pateamine A. Other studies and ...

 Related Synthetic Route
1,1,1-trichloro-2-methylpropan-2-yl ((12Z,3S,6Z,8E,11S,15R,17S)-3-((1E,3E,5E)-7-(dimethylamino)-2,5-dimethylhepta-1,3,5-trien-1-yl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-1(2,4)-thiazolacycloheptadecaphane-6,8-dien-15-yl)carbamate Structure

201339-93-7

1,1,1-trichloro...

~75%

Pateamine A Structure

139220-18-1

Pateamine A

(S,E)-tert-butyl((5-iodo-4-methylpent-4-en-2-yl)oxy)dimethylsilane Structure

218782-56-0

(S,E)-tert-buty...

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

201340-04-7

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

ethyl (R,E)-2-(4-bromo-2-((triisopropylsilyl)oxy)pent-3-en-1-yl)thiazole-4-carboxylate Structure

201340-00-3

ethyl (R,E)-2-(...

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-65-1

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

201340-09-2

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

(S)-3-(2-((R,E)-4-bromo-2-((triisopropylsilyl)oxy)pent-3-en-1-yl)thiazol-4-yl)-N-methoxy-N-methylbutanamide Structure

201340-03-6

(S)-3-(2-((R,E)...

~%

Pateamine A Structure

139220-18-1

Pateamine A

Structure

609823-27-0

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

201340-05-8

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

tert-butyl ((3S,11S,15R,17S,E)-3-((E)-2-bromoprop-1-en-1-yl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]henicosa-1(21),8,18-trien-6-yn-15-yl)carbamate Structure

201340-07-0

tert-butyl ((3S...

~%

Pateamine A Structure

139220-18-1

Pateamine A

Structure

218782-80-0

~%

Pateamine A Structure

139220-18-1

Pateamine A

(S)-3-((S)-3-(2-((R,E)-4-bromo-2-((triisopropylsilyl)oxy)pent-3-en-1-yl)thiazol-4-yl)butanoyl)-4-phenyloxazolidin-2-one Structure

201340-11-6

(S)-3-((S)-3-(2...

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-84-4

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

(S)-3-((E)-3-(2-((R,E)-4-bromo-2-((triisopropylsilyl)oxy)pent-3-en-1-yl)thiazol-4-yl)acryloyl)-4-phenyloxazolidin-2-one Structure

218782-69-5

(S)-3-((E)-3-(2...

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-77-5

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-83-3

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-86-6

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-85-5

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

N/A Structure

218782-76-4

N/A

~%

Pateamine A Structure

139220-18-1

Pateamine A

1,1,1-trichloro-2-methylpropan-2-yl ((12Z,3S,6Z,8E,11S,15R,17S)-3-((E)-2-bromoprop-1-en-1-yl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-1(2,4)-thiazolacycloheptadecaphane-6,8-dien-15-yl)carbamate Structure

201340-08-1

1,1,1-trichloro...

~%

Pateamine A Structure

139220-18-1

Pateamine A

Dimethylamine Structure

124-40-3

Dimethylamine

Tosyl chloride Structure

98-59-9

Tosyl chloride

~%

2-Penten-4-yn-1-amine,N,N,3-trimethyl-,(2E)-(9CI) Structure

201339-97-1

2-Penten-4-yn-1...


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