A concise formal stereoselective total synthesis of (-)-swainsonine

被引：26

作者：

Wang, Xiao-Gang ^{[1
,2
]}

Wang, Ai-E ^{[1
,2
,3
]}

Huang, Pei-Qiang ^{[1
,2
,3
]}

机构：

[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China

[2] Xiamen Univ, Fujian Prov Key Lab Chem Biol, Xiamen 361005, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 02期

关键词：

Indolizidines; Alkaloids; alpha-Amidoalkylation; Building blocks; Stereoselective synthesis; RING-CLOSING METATHESIS; INTERMOLECULAR ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; SWAINSONINE; ALKALOIDS; IONS; (+)-SWAINSONINE; TRANSFORMATION; DERIVATIVES; ALKYLATION;

D O I：

10.1016/j.cclet.2013.12.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short formal stereoselective synthesis of (-)-swainsonine (1) is described. Our synthesis started with the versatile building block (R)-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley's-sulfone chemistry (N-alpha-sulfonylation and ZnCl2-catalyzed N-alpha-amidovinylation), an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine (8R,8aS)-3 has been achieved in five steps. The indolizidine (8R,8aS)-3 is an advanced intermediate toward the synthesis of (-)-swainsonine (1). (C) 2013 Pei-Qiang Huang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：193 / 196

页数：4

共 50 条

[1] A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton [J].

Archibald, Glenn ;

Lin, Chih-Pei ;

Boyd, Peter ;

Barker, David ;

Caprio, Vittorio .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) :7968-7980

[2] Asymmetric synthesis of anti-1,2-amino alcohols via the Borono-Mannich reaction:: A formal synthesis of (-)-swainsonine [J].

Au, Christopher W. G. ;

Pyne, Stephen G. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :7097-7099

[3] A Formal Synthesis of Swainsonine by Gold-Catalyzed Allene Cyclization [J].

Bates, Roderick W. ;

Dewey, Mark R. .

ORGANIC LETTERS, 2009, 11 (16) :3706-3708

[4] SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE [J].

BROWN, DS ;

CHARREAU, P ;

HANSSON, T ;

LEY, SV .

TETRAHEDRON, 1991, 47 (07) :1311-1328

[5] A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement [J].

Buschmann, N ;

Rückert, A ;

Blechert, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4325-4329

[6]

Chen H, 2009, CHINESE J ORG CHEM, V29, P703

[7] Progress on the total synthesis of natural products in China: From 2006 to 2010 [J].

Chen Jie ;

Wang AiE ;

Huo HaoHua ;

Huang PeiQiang .

SCIENCE CHINA-CHEMISTRY, 2012, 55 (07) :1175-1212

[8] Radical cyclizations of acylsilanes in the synthesis of (+)-swainsonine and formal synthesis of (-)-epiquinamide [J].

Chen, Ming-Jen ;

Tsai, Yeun-Min .

TETRAHEDRON, 2011, 67 (08) :1564-1574

[9] A formal synthesis of (-)-swainsonine from a chiral aziridine [J].

Choi, Hwan Geun ;

Kwon, Ji Hye ;

Kim, Jong Chan ;

Lee, Won Koo ;

Eum, Heesung ;

Ha, Hyun-Joon .

TETRAHEDRON LETTERS, 2010, 51 (25) :3284-3285

[10] SPECTROSCOPIC INVESTIGATION OF SWAINSONINE - ALPHA-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA-CANESCENS [J].

COLEGATE, SM ;

DORLING, PR ;

HUXTABLE, CR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2257-2264

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