Synthesis of the carbocyclic core of zoanthenol: Implementation of an unusual acid-catalyzed cyclization

被引：46

作者：

Behenna, Douglas C. ^{[1
]}

Stockdill, Jennifer L. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synth, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 22期

关键词：

alkaloids; asymmetric catalysis; cyclization; natural products;

D O I：

10.1002/anie.200700430

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A smokin' hot cyclization! When the racemic cyclization precursor is heated in neat trifluoroacetic acid, an unusual Friedel-Crafts-type cyclization forms the carbocyclic core of the marine alkaloid zoanthenol containing two all-carbon-substituted quaternary centers. Catalytic asymmetric alkylation allows entry into an enantioselective route. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4077 / 4080

页数：4

共 29 条

[1] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[2] New alkaloids from a marine zoanthid [J].

Daranas, AH ;

Fernández, JJ ;

Gavín, JA ;

Norte, M .

TETRAHEDRON, 1999, 55 (17) :5539-5546

[3] TOTAL SYNTHESIS OF 2,3-DIHYDROILLUDINE-M BY CYCLOADDITION OF ENAMINE TO CYCLOPROPENE [J].

FRANCKNEUMANN, M ;

MIESCH, M ;

BARTH, F .

TETRAHEDRON, 1993, 49 (07) :1409-1420

[4]

Hikage N, 2000, CHEM PHARM BULL, V48, P1370

[5] Synthetic studies of zoanthamine/norzoanthamine alkaloids: Construction of the heterocyclic aminal core (CDEFG ring) [J].

Hikage, N ;

Furukawa, H ;

Takao, K ;

Kobayashi, S .

TETRAHEDRON LETTERS, 1998, 39 (34) :6241-6244

[6] Synthetic studies of zoanthamine/norzoanthamine alkaloids: Advanced intermediate for the heterocyclic aminal core [J].

Hikage, N ;

Furukawa, H ;

Takao, K ;

Kobayashi, S .

TETRAHEDRON LETTERS, 1998, 39 (34) :6237-6240

[7] Synthesis of the zoanthamine ABC ring system: Some surprises from intramolecular Diels-Alder reactions [J].

Juhl, M ;

Nielsen, TE ;

Le Quement, S ;

Tanner, D .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :265-280

[8]

Kuramoto M., 1996, 38 S CHEM NAT PROD, P79

[9] A SYNTHESIS OF THE ABIETANE DITERPENOID QUINONE (+/-)-ROYLEANONE VIA MALEOYLCOBALT TECHNOLOGY [J].

LIEBESKIND, LS ;

CHIDAMBARAM, R ;

NIMKAR, S ;

LIOTTA, D .

TETRAHEDRON LETTERS, 1990, 31 (26) :3723-3726

[10] Efficient synthesis of benzocyclohexanes via intramolecular Friedel-Crafts reaction of halogen free 6-acetoxy-4-alkenyl arenes [J].

Ma, SM ;

Zhang, JL .

TETRAHEDRON LETTERS, 2002, 43 (18) :3435-3438

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