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

Journal of the American Chemical Society

Total synthesis of (-)-domoic acid. A revision of the original structure

Y Ohfune, M Tomita

Index: Journal of the American Chemical Society, , vol. 104, # 12 p. 3511 - 3513

Full Text: HTML

Citation Number: 218

Abstract

... We also thank Dr. William F. Johns of the GD Searle Co. for arranging for us to receive the various authentic specimens of spironolactone and related substances that were used in this study. ... 0002-7863/82/1504-3511$01.25/0 0 1982 American Chemical Society ... Soc., Vol. ...

 Related Synthetic Route
Boc-Pyr-OH Structure

53100-44-0

Boc-Pyr-OH

~%

Boc-L-Pyroglutaminol Structure

81658-25-5

Boc-L-Pyroglutaminol

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L-glutamic acid Structure

56-86-0

L-glutamic acid

~%

Boc-L-Pyroglutaminol Structure

81658-25-5

Boc-L-Pyroglutaminol

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tert-butyl (2S,3S,4S)-4-((S)-1-(1,3-dioxolan-2-yl)ethyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

81658-31-3

tert-butyl (2S,...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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(2S,3S,4S)-1-tert-butyl 2-methyl 3-(2-methoxy-2-oxoethyl)-4-((R)-1-oxopropan-2-yl)pyrrolidine-1,2-dicarboxylate Structure

81658-33-5

(2S,3S,4S)-1-te...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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N/A Structure

81802-30-4

N/A

~%

Domoic acid Structure

14277-97-5

Domoic acid

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1-(tert-butyl) 2-methyl (2S,3S,4R)-3-(2-methoxy-2-oxoethyl)-4-(4-methoxybut-3-en-2-yl)pyrrolidine-1,2-dicarboxylate Structure

81658-34-6

1-(tert-butyl) ...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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1-(tert-butyl) 2-methyl (2S,3S,4S)-4-((S)-1-(1,3-dioxolan-2-yl)ethyl)-3-(2-methoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

81658-32-4

1-(tert-butyl) ...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(4-oxo-3-(phenylselanyl)butan-2-yl)pyrrolidine-1,2-dicarboxylate Structure

81658-35-7

1-(tert-butyl) ...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-((Z)-4-oxobut-2-en-2-yl)pyrrolidine-1,2-dicarboxylate Structure

81658-36-8

1-(tert-butyl) ...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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tert-butyl (3S,4S,5S)-3-((S)-1-(1,3-dioxolan-2-yl)ethyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-methoxy-2-oxoethyl)-2-oxopyrrolidine-1-carboxylate Structure

81658-29-9

tert-butyl (3S,...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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(R,3E,5Z)-6-((3S,4S,5S)-1-(tert-butoxycarbonyl)-4-(2-methoxy-2-oxoethyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-2-methylhepta-3,5-dienoic acid Structure

81658-41-5

(R,3E,5Z)-6-((3...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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1-(tert-butyl) 2-methyl (2S,3S,4S)-4-((R,2Z,4E)-7-hydroxy-6-methylhepta-2,4-dien-2-yl)-3-(2-methoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

81703-63-1

1-(tert-butyl) ...

~%

Domoic acid Structure

14277-97-5

Domoic acid

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Boc-L-Pyroglutaminol Structure

81658-25-5

Boc-L-Pyroglutaminol

~%

Boc-Pyr-OH Structure

53100-44-0

Boc-Pyr-OH

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L-glutamic acid Structure

56-86-0

L-glutamic acid

~%

Boc-Pyr-OH Structure

53100-44-0

Boc-Pyr-OH

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Detail Synthetic Route


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