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

Total synthesis of the Cephalotaxus alkaloids. Cephalotaxine, cephalotaxinone, and demethylcephalotaxinone

SM Weinreb, J Auerbach

Index: Weinreb; Auerbach Journal of the American Chemical Society, 1975 , vol. 97, # 9 p. 2503 - 2506

Full Text: HTML

Citation Number: 80

Abstract

Abstract: Cephalotaxine (l), the major alkaloid produced by several species of Cephalotaxus (plum-yews), has been synthesized as its racemate in eight steps from 1-prolinol (4) and 3, 4- methylenedioxyphenylacetyl chloride (3). Cephalotaxinone (22) and demethylcephalotaxinone (19), minor alkaloids which normally occur with cephalotaxine, have been prepared as intermediates in this synthesis.

1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde Structure

1-(benzo[1,3]di...

~%

2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-acetoxy-1-(5,...

5,8,9,10-tetrahydro-6h-[1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-6-one Structure

5,8,9,10-tetrah...

~%

2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-acetoxy-1-(5,...

2-Acetoxypropionyl Chloride Structure

2-Acetoxypropio...

5,8,9,10-tetrahydro-6H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine Structure

5,8,9,10-tetrah...

~%

2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-acetoxy-1-(5,...

1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde Structure

1-(benzo[1,3]di...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

5,8,9,10-tetrahydro-6h-[1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-6-one Structure

5,8,9,10-tetrah...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

5,8,9,10-tetrahydro-6H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine Structure

5,8,9,10-tetrah...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

2-hydroxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-hydroxy-1-(5,...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-acetoxy-1-(5,...

~%

4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol,1,5,6,8,9,14b-hexahydro-2-methoxy-, (1R,3aS,14bR)-rel- Structure

4H-Cyclopenta[a...

1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde Structure

1-(benzo[1,3]di...

~%

5,8,9,10-tetrahydro-6h-[1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-6-one Structure

5,8,9,10-tetrah...

1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde Structure

1-(benzo[1,3]di...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

5,8,9,10-tetrahydro-6h-[1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-6-one Structure

5,8,9,10-tetrah...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-acetoxy-1-(5,...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

5,8,9,10-tetrahydro-6H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine Structure

5,8,9,10-tetrah...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

Pyruvic acid Structure

5,8,9,10-tetrahydro-6H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine Structure

5,8,9,10-tetrah...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...

2-hydroxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one Structure

2-hydroxy-1-(5,...

~%

1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione Structure

1-(5,8,9,10-tet...