Vinylogous Mannich reactions. Stereoselective formal synthesis of pumiliotoxin 251D

被引：57

作者：

Martin, SF ^{[1
]}

Bur, SK ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

Mannich reactions; iminium ions; asymmetric synthesis; alkaloids;

D O I：

10.1016/S0040-4020(99)00452-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of (-)-3, a known precursor of pumiliotoxin 251D, has been completed using a vinylogous Mannich reaction as a key construction. Silyloxyfuran PO added to methoxy pyrrolidine 20 in the presence of TMS-OTf to give a mixture (4.8:1) of 21 and 22 in 57% yield. Reduction and global deprotection of 21 afforded the bicyclic lactam 23. Raney Nickel mediated extrusion of the hydroxymethyl group from 23 gave (-)-3. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：8905 / 8914

页数：10

相关论文

共 38 条

[1]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[2]

2-E

[3] Stereospecific synthesis of (2S,4R)-[5,5,5-H-2(3)]leucine [J].

August, RA ;

Khan, JA ;

Moody, CM ;

Young, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (06) :507-514

[4] TOXICITY OF PUMILIOTOXIN 251D AND SYNTHETIC ANALOGS TO THE COTTON PEST HELIOTHIS-VIRESCENS [J].

BARGAR, TM ;

LETT, RM ;

JOHNSON, PL ;

HUNTER, JE ;

CHANG, CP ;

PERNICH, DJ ;

SABOL, MR ;

DICK, MR .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (04) :1044-1051

[5] A formal synthesis of pumiliotoxin 251D, via a highly diastereoselective addition of a titanium homoenolate to an L-proline derivative [J].

Barrett, AGM ;

Damiani, F .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1410-1411

[6] FURAN-BASED, PYRROLE-BASED, AND THIOPHENE-BASED SILOXYDIENES FOR SYNTHESES OF DENSELY FUNCTIONALIZED HOMOCHIRAL COMPOUNDS [J].

CASIRAGHI, G ;

RASSU, G .

SYNTHESIS-STUTTGART, 1995, (06) :607-626

[7] THE 4-CARBON ELONGATION OF 3-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN - HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE 7-CARBON ALPHA,BETA-UNSATURATED 2,3-DIDEOXY-ALDONOLACTONES [J].

CASIRAGHI, G ;

COLOMBO, L ;

RASSU, G ;

SPANU, P ;

FAVA, GG ;

BELICCHI, MF .

TETRAHEDRON, 1990, 46 (16) :5807-5824

[8] Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones:: asymmetric synthesis of (-)-perhydrohistrionicotoxin [J].

Comins, DL ;

Zhang, YM ;

Zheng, XL .

CHEMICAL COMMUNICATIONS, 1998, (22) :2509-2510

[9]

Cossy J, 1997, B SOC CHIM FR, V134, P141

[10] NEW CLASS OF INDOLIZIDINE ALKALOIDS FROM THE POISON FROG, DENDROBATES-TRICOLOR - X-RAY-ANALYSIS OF 8-HYDROXY-8-METHYL-6-(2'-METHYLHEXYLIDENE)-1-AZABICYCLO[4.3.0]NONANE [J].

DALY, JW ;

TOKUYAMA, T ;

FUJIWARA, T ;

HIGHET, RJ ;

KARLE, IL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :830-836

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