Studies on the narciclasine alkaloids: total synthesis of (+)-narciclasine and (+)-pancratistatin

JH Rigby, USM Maharoof…

Index: Journal of the American Chemical Society, , vol. 122, # 28 p. 6624 - 6628

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Citation Number: 112

Abstract

... Journal of the American ... from the Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489. J. Am. Chem. Soc. , 2000, 122 (28), pp 6624–6628. DOI: 10.1021/ja000930i. Publication Date (Web): June 29, 2000. Copyright © 2000 American Chemical ...

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2,4-Cyclohexadien-1-carbonsaeure-methylester Structure

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2,4-Cyclohexadi...

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Narciclasine Structure

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Narciclasine

bromo-5 hydroxy-4 benzodioxole-1,3 Structure

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bromo-5 hydroxy...

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Narciclasine Structure

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Narciclasine Structure

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(+)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo[4,1,0]hept-3-ene-4-carboxylate Structure

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(+)-methyl (1β,...

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Narciclasine Structure

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Narciclasine

5-bromo-4-(1-ethoxyethoxy)-2H-benzo[d]1,3-dioxolane Structure

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Narciclasine Structure

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Narciclasine

methyl 5-(butyryloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate Structure

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methyl 5-(butyr...

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Narciclasine Structure

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N/A

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Narciclasine Structure

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Narciclasine

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N/A

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Narciclasine Structure

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Narciclasine

(+)-5-(tert-butyl-dimethylsilanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester Structure

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(+)-5-(tert-but...

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Narciclasine Structure

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Narciclasine

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Narciclasine Structure

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Narciclasine

(3aS,3bR,12S,12aR)-6,12-dihydroxy-4-(4-methoxybenzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydrobis([1,3]dioxolo)[4,5-c:4',5'-j]phenanthridin-5(3aH)-one Structure

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(3aS,3bR,12S,12...

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Narciclasine Structure

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Narciclasine

N-((1R,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-4-hydroxy-N-(4-methoxybenzyl)benzo[d][1,3]dioxole-5-carboxamide Structure

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N-((1R,5S,6R)-5...

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Narciclasine Structure

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Narciclasine

(1S,2R,4aS,11bR)-1-((tert-butyldimethylsilyl)oxy)-2,7-dihydroxy-5-(4-methoxybenzyl)-1,4a,5,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one Structure

200182-38-3

(1S,2R,4aS,11bR...

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Narciclasine Structure

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Narciclasine

(6aS,7aR,8aR,9S,9aR)-9-((tert-butyldimethylsilyl)oxy)-4-hydroxy-6-(4-methoxybenzyl)-6a,7,7a,8a,9,9a-hexahydro-[1,3]dioxolo[4,5-j]oxireno[2,3-b]phenanthridin-5(6H)-one Structure

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(6aS,7aR,8aR,9S...

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Narciclasine Structure

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Narciclasine

(3aS,3bR,12S,12aR)-4-(4-methoxybenzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,12,12a-hexahydrobis([1,3]dioxolo)[4,5-c:4',5'-j]phenanthridine-6,12-diyl diacetate Structure

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(3aS,3bR,12S,12...

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Narciclasine Structure

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Narciclasine

N/A Structure

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N/A

~%

Narciclasine Structure

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Narciclasine

N/A Structure

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N/A

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Narciclasine Structure

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Narciclasine

N/A Structure

200182-35-0

N/A

~%

Narciclasine Structure

29477-83-6

Narciclasine

(3aS,3bR,10bR,11S,12R,12aS)-11-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydrobis([1,3]dioxolo)[4,5-c:4',5'-j]phenanthridine-6,12-diyl diacetate Structure

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(3aS,3bR,10bR,1...

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Narciclasine Structure

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Narciclasine

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2,3-(methylened...

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Narciclasine Structure

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2,3-Dihydroxybe...

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