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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者10.1002/anie.201600521

Enantioselective total synthesis of (-)-taxol

…, S Kawahara, T Nishimori, H Kashima…

文献索引：Kusama, Hiroyuki; Hara, Ryoma; Kawahara, Shigeru; Nishimori, Toshiyuki; Kashima, Hajime; Nakamura, Nobuhito; Morihira, Koichiro; Kuwajima, Isao Journal of the American Chemical Society, 2000 , vol. 122, # 16 p. 3811 - 3820

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被引用次数: 145

摘要

Enantioselective total synthesis of taxol has been accomplished. Coupling reaction of the optically pure A-ring hydroxy aldehyde with the aromatic C-ring fragment followed by Lewis acid mediated eight-membered B-ring cyclization gave the desired ABC endo-tricarbocycle. The C-ring moiety of this product was reduced under Birch conditions to the cyclohexadiene derivative, which was oxygenated by singlet oxygen from the convex β-face to give the ...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,3a1S,6aS,7S,8S,10S,13aS)-10-((tert-butyldimethylsilyl)oxy)-7,8-dihydroxy-11,14,14-trimethyl-4,5,7,8,9,10,13,13a-octahydro-1,3-dioxa-3a1,6a:8,12-dimethanocyclodeca[de]naphthalene-2,6(3aH)-dione结构式

(3aS,3a1S,6aS,7...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,5S,9S,9aS,10S,13bS)-5-((tert-butyldimethylsilyl)oxy)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9,9a,10,11,12,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-9,10,13-triol结构式

(2S,3aS,5S,9S,9...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,5S,9S,9aS,10S,13aS,13bS)-5-((tert-butyldimethylsilyl)oxy)-9,10-dihydroxy-6,15,15-trimethyl-2-phenyl-4,5,8,9,11,12-hexahydro-13bH-3a,7:9a,13a-dimethanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13(10H)-one结构式

(2S,3aS,5S,9S,9...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,5S,9S,9aS,10S,13aS,13bS)-2,2-di-tert-butyl-5-((tert-butyldimethylsilyl)oxy)-9,10-dihydroxy-6,15,15-trimethyl-4,5,8,9,11,12-hexahydro-13bH-3a,7:9a,13a-dimethanobenzo[3,4]cyclodeca[1,2-d][1,3,2]dioxasilol-13(10H)-one结构式

(3aS,5S,9S,9aS,...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,3a1S,7S,8aS,11aS,11bS,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalene-2,12(13H)-dione结构式

(3aS,3a1S,7S,8a...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,7S,8aS,11aS,12R,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,15,15-trimethyl-2-phenyl-3a,7,8,11a,12,13,14,14a-octahydro-4H-1,3,9,11-tetraoxa-10-sila-5,8a-methanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-ol结构式

(3aS,7S,8aS,11a...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,3a1S,7S,8aS,11aS,11bS,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-2-phenyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12(13H)-one结构式

(2S,3aS,3a1S,7S...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,5S,9S,9aS,10S,13aR,13bS)-5,9,10-trihydroxy-6,9a,14,14-tetramethyl-2-phenyl-4,5,8,9,9a,10,11,12,13a,13b-decahydro-13H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-one结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,5S,9aS,10S,13aR,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9a,10,11,12,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-9,13-dione结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2S,3aS,5S,9aS,10S,13aR,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-9-oxo-2-phenyl-5,8,9,9a,10,11,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl trifluoromethanesulfonate结构式

(2S,3aS,5S,9aS,...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

((2S,3aS,3a1R,7S,8aS,10S,11aS,14aS)-7,12-bis((tert-butyldimethylsilyl)oxy)-2-(4-methoxyphenyl)-6,15,15-trimethyl-10-phenyl-3a,4,7,8,11a,13,14,14a-octahydro-3a1H-1,3,9,11-tetraoxa-5,8a-methanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-3a1-yl)methanol结构式

((2S,3aS,3a1R,7...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,3a1S,7S,8aS,10S,11aS,11bR,14aS)-7-hydroxy-3a1,6,15,15-tetramethyl-2,10-diphenyl-3a,3a1,4,7,8,11a,11b,13,14,14a-decahydro-12H-1,3,9,11-tetraoxa-2-bora-5,8a-methanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-one结构式

(3aS,3a1S,7S,8a...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(3aS,3a1S,7S,8aS,10S,11aS,11bR,14aS)-7-((tert-butyldimethylsilyl)oxy)-3a1,6,15,15-tetramethyl-2,10-diphenyl-3a,3a1,4,7,8,11a,11b,13,14,14a-decahydro-12H-1,3,9,11-tetraoxa-2-bora-5,8a-methanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-one结构式

(3aS,3a1S,7S,8a...

~%

7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-((tert-butyldimethylsilyl)oxy)-11,12,12b-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-6-yl acetate结构式

(2aR,4S,4aS,6R,...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9-((tert-butyldimethylsilyl)oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate结构式

(2aR,4S,4aS,6R,...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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~84%

紫杉醇结构式

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7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...