Concise Total Synthesis of (±)-Pseudotabersonine via Double Ring-Closing Metathesis Strategy

被引：36

作者：

Cheng, Bo ^{[1
]}

Sunderhaus, James D. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 16期

基金：

美国国家卫生研究院;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; MANZAMINE-A; ALKALOIDS; CONSTRUCTION; INDOLE;

D O I：

10.1021/ol101356u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of (+/-)-pseudotabersonine from commercially available 1-(phenylsulfonyl)-3-indolecarboxaldehyde has been accomplished. This synthesis features the convergent assembly of a key intermediate via a stepwise variant of a Mannich-type multicomponent coupling process, a double ring-closing metathesis, and a one-pot deprotection/cyclization reaction.

引用

页码：3622 / 3625

页数：4

共 39 条

[1]

Alvaro G, 2000, SYNTHESIS-STUTTGART, P581

[2] Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine [J].

Andrade, RB ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (25) :5733-5735

[3] Diels-Alder reactions of N-tosyl-3-nitroindole and dienamides:: synthesis of intermediates of Aspidospermine alkaloids [J].

Biolatto, B ;

Kneeteman, M ;

Mancini, P .

TETRAHEDRON LETTERS, 1999, 40 (17) :3343-3346

[4] A COMMON INTERMEDIATE PROVIDING SYNTHESES OF PSI-TABERSONINE, CORONARIDINE, IBOXYPHYLLINE, IBOPHYLLIDINE, VINAMIDINE, AND VINBLASTINE [J].

BORNMANN, WG ;

KUEHNE, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1752-1760

[5] Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis [J].

Brenneman, JB ;

Machauer, R ;

Martin, SF .

TETRAHEDRON, 2004, 60 (34) :7301-7314

[6] BIOMIMETIC TOTAL SYNTHESIS OF PSEUDOTABERSONINE - A NOVEL OXINDOLE-BASED APPROACH TO CONSTRUCTION OF ASPIDOSPERMA ALKALOIDS [J].

CARROLL, WA ;

GRIECO, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1164-1165

[7]

Cordell G.A., 1979, ALKALOIDS, V17, P199

[8]

COURTOIS G, 1986, B SOC CHIM FR, P449

[9] Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis [J].

Deck, Jason A. ;

Martin, Stephen F. .

ORGANIC LETTERS, 2010, 12 (11) :2610-2613

[10] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

← 1 2 3 4 →