Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids

被引：66

作者：

He, Weigang ^{[1
]}

Hu, Jiadong ^{[1
]}

Wang, Pengyan ^{[1
]}

Chen, Le ^{[1
]}

Ji, Kai ^{[1
]}

Yang, Siyu ^{[1
]}

Li, Yin ^{[1
]}

Xie, Zhilong ^{[1
]}

Xie, Weiqing ^{[1
,2
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 14期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; indole alkaloids; Michael addition; oxindoles; synthetic methods; NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; ASYMMETRIC ALLYLIC SUBSTITUTION; AZA-COPE REARRANGEMENTS; RECENT PROGRESS; (+/-)-DEHYDROTUBIFOLINE; (-)-TUBIFOLINE; (+/-)-AKUAMMICINE; SPIROOXINDOLES; CHEMISTRY;

D O I：

10.1002/anie.201800567

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N-dioxide Sc(OTf)(3) catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] was achieved in 10-11 steps.

引用

页码：3806 / 3809

页数：4

共 66 条

[1] NUCLEOPHILIC-ADDITION OF INDOLE-2-ACETIC ESTER ENOLATES TO N-ALKYLPYRIDINIUM SALTS - A FORMAL SYNTHESIS OF THE STRYCHNOS ALKALOIDS TUBIFOLIDINE AND TUBIFOLINE [J].

ALVAREZ, M ;

SALAS, M ;

DEVECIANA, A ;

LAVILLA, R ;

BOSCH, J .

TETRAHEDRON LETTERS, 1990, 31 (35) :5089-5092

[2] An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline [J].

Amat, M ;

Coll, MD ;

Passarella, D ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2775-2778

[3] SYNTHESIS AND NMR DATA OF THE STRYCHNOS INDOLE ALKALOID TUBIFOLINE [J].

AMAT, M ;

LINARES, A ;

MUNOZ, J ;

BOSCH, J .

TETRAHEDRON LETTERS, 1988, 29 (48) :6373-6376

[4] A NEW STRATEGY FOR THE SYNTHESIS OF PENTACYCLIC STRYCHNOS ALKALOIDS - SYNTHESIS OF (+/-)-TUBIFOLIDINE [J].

AMAT, M ;

LINARES, A ;

SALAS, ML ;

ALVAREZ, M ;

BOSCH, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (06) :420-421

[5] Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine [J].

Amat, M ;

Coll, MD ;

Bosch, J ;

Espinosa, E ;

Molins, E .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :935-948

[6]

ANGENOT L, 1978, Plantes Medicinales et Phytotherapie, V12, P123

[7] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .24. THE AZA-COPE-MANNICH APPROACH TO STRYCHNOS ALKALOIDS - SHORT STEREOCONTROLLED TOTAL SYNTHESES OF (+/-)-DEHYDROTUBIFOLINE AND (+/-)-AKUAMMICINE [J].

ANGLE, SR ;

FEVIG, JM ;

KNIGHT, SD ;

MARQUIS, RW ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3966-3976

[8]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[9]

[Anonymous], 2013, ANGEW CHEM

[10]

[Anonymous], 2013, ANGEW CHEM, V125, P13162

← 1 2 3 4 5 6 7 →