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

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified RambergľBäcklund reaction

…, Y Zhang, Z Huang, X Cao, K Gao

Index: Li, Yang; Zhang, Yu; Huang, Zhi; Cao, Xiaoping; Gao, Kun Canadian Journal of Chemistry, 2004 , vol. 82, # 5 p. 622 - 630

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Citation Number: 14

Abstract

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a ľ 1n by the recently developed one-flask RambergľBäcklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of ...

piperonal Structure

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPIONALDEHYDE Structure

3-BENZO[1,3]DIO...

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPIONALDEHYDE Structure

3-BENZO[1,3]DIO...

trans-3,4-Methylenedioxycinnamyl alcohol Structure

trans-3,4-Methy...

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPIONALDEHYDE Structure

3-BENZO[1,3]DIO...

Isobutylamine Structure

Chloroacetyl chloride Structure

Chloroacetyl ch...

~98%

Acetamide,2-chloro-N-(2-methylpropyl)- Structure

Acetamide,2-chl...

2-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]-N-isobutylacetamide Structure

2-[(E)-3,4-(met...

~85%

Piperlonguminine Structure

Piperlonguminine

piperonal Structure

~%

Piperlonguminine Structure

Piperlonguminine

(E)-S-(3-(benzo[d][1,3]dioxol-5-yl)allyl) ethanethioate Structure

(E)-S-(3-(benzo...

~%

Piperlonguminine Structure

Piperlonguminine

2-[(E)-3,4-(methylenedioxy)cinnamylthio]-N-isobutylacetamide Structure

2-[(E)-3,4-(met...

~%

Piperlonguminine Structure

Piperlonguminine

trans-3,4-Methylenedioxycinnamyl alcohol Structure

trans-3,4-Methy...

~%

Piperlonguminine Structure

Piperlonguminine

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

Piperlonguminine Structure

Piperlonguminine

Piperidine Structure

Chloroacetyl chloride Structure

Chloroacetyl ch...

~98%

Ethanone,2-chloro-1-(1-piperidinyl)- Structure

Ethanone,2-chlo...

1-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]acetyl-pyrrolidine Structure

1-[(E)-3,4-(met...

~82%

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one Structure

(2E,4E)-5-(1,3-...

trans-3,4-Methylenedioxycinnamyl alcohol Structure

trans-3,4-Methy...

~%

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one Structure

(2E,4E)-5-(1,3-...

(E)-S-(3-(benzo[d][1,3]dioxol-5-yl)allyl) ethanethioate Structure

(E)-S-(3-(benzo...

~%

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one Structure

(2E,4E)-5-(1,3-...

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one Structure

(2E,4E)-5-(1,3-...

3-phenylpropyl benzenesulfonate Structure

3-phenylpropyl ...

~97%

5-(1,3-benzodioxol-5-yl)pentan-1-ol Structure

5-(1,3-benzodio...

piperonal Structure

~%

5-(1,3-benzodioxol-5-yl)pentan-1-ol Structure

5-(1,3-benzodio...

all-trans-5-(3,4-Methylendioxyphenyl)-2,4-pentadiensaeureethylester Structure

all-trans-5-(3,...

~%

5-(1,3-benzodioxol-5-yl)pentan-1-ol Structure

5-(1,3-benzodio...

1-[(2E)-octenylsulfonyl]acetyl-pyrrolidine Structure

1-[(2E)-octenyl...

~86%

Sarmentine Structure

(E)-S-(oct-2-en-1-yl) ethanethioate Structure

(E)-S-(oct-2-en...

~%

Sarmentine Structure

1-[(2E)-octenylthio]acetyl-pyrrolidine Structure

1-[(2E)-octenyl...

~%

Sarmentine Structure

ethyl 2-octenoate Structure

ethyl 2-octenoate

~%

Sarmentine Structure

Trans-2-Octen-1-ol Structure

Trans-2-Octen-1-ol

~%

Sarmentine Structure

Hexanal Structure

~%

Sarmentine Structure

2-[(2E,4E)-5-(2-thienyl)-pentadienylsulfonyl]-N-isobutylacetamide Structure

2-[(2E,4E)-5-(2...

~36%

N-(2-methylpropyl)-7-thiophen-2-ylhepta-2,4,6-trienamide Structure

N-(2-methylprop...

2-[(2E,4E)-5-(2-thienyl)-pentadienylthio]-N-isobutylacetamide Structure

2-[(2E,4E)-5-(2...

~%

N-(2-methylpropyl)-7-thiophen-2-ylhepta-2,4,6-trienamide Structure

N-(2-methylprop...

Pyrrolidine Structure

Chloroacetyl chloride Structure

Chloroacetyl ch...

~99%

2-chloro-1-pyrrolidin-1-yl-ethanone Structure

2-chloro-1-pyrr...

1-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]acetyl-piperidine Structure

1-[(E)-3,4-(met...

~79%

Piperine Structure

piperonal Structure

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPAN-1-OL Structure

3-BENZO[1,3]DIO...

ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate Structure

ethyl (E)-3-(1,...

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPAN-1-OL Structure

3-BENZO[1,3]DIO...

trans-3,4-Methylenedioxycinnamyl alcohol Structure

trans-3,4-Methy...

~%

3-BENZO[1,3]DIOXOL-5-YL-PROPAN-1-OL Structure

3-BENZO[1,3]DIO...

Hexanal Structure

~%

Pellitorine Structure

ethyl 2-octenoate Structure

ethyl 2-octenoate

~%

Pellitorine Structure

Trans-2-Octen-1-ol Structure

Trans-2-Octen-1-ol

~%

Pellitorine Structure

(E)-S-(oct-2-en-1-yl) ethanethioate Structure

(E)-S-(oct-2-en...

~%

Pellitorine Structure

2-[(2E)-octenylthio]-N-isobutylacetamide Structure

2-[(2E)-octenyl...

~%

Pellitorine Structure

Lewis base-promoted hydrosilylation of cyclic malonates: Syn...

[Frost, Christopher G.; Hartley, Benjamin C. Organic Letters, 2007 , vol. 9, # 21 p. 4259 - 4261]

Ruthenium-catalyzed cycloisomerization of cis-3-En-1-ynes to...

[Datta, Swarup; Odedra, Arjan; Liu, Rai-Shung Journal of the American Chemical Society, 2005 , vol. 127, # 33 p. 11606 - 11607]

Three-component synthesis of (E)-α, β-unsaturated amides of ...

[Schobert; Siegfried; Gordon Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 19 p. 2393 - 2397]