A SYNTHESIS OF (+)-PEDERIN - THE METALATED DIHYDROPYRAN APPROACH

被引：26

作者：

JAROWICKI, K ^{[1
]}

KOCIENSKI, P ^{[1
]}

MARCZAK, S ^{[1
]}

WILLSON, T ^{[1
]}

机构：

[1] UNIV SOUTHAMPTON,DEPT CHEM,SOUTHAMPTON SO9 5NH,HANTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)97415-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of a 6-lithio-3,4-dihydro-2H-pyran to a methyl oxamate ester in the preseuce of TMEDA is a key step in the synthesis of a masked 1,2,3-tricarbonyl moiety used to construct the N-(1-alkoxy-1-alkyl)-amide bridge of the potent cytotoxic agent pederin. A Pd(0)-catalysed stannylation of an O-trifluoromethylsulfonyl ketene acetal provides an efficieat synthesis of the 6-(trimethylstannyl)-3,4-dihydro-2H-pyran which transmetallates to the lithium daivative on treatment with n-BuLi. © 1990.

引用

页码：3433 / 3436

页数：4

共 23 条

[1] CYCLIC VINYL ETHER CARBANIONS .2. PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL-COMPOUNDS [J].

BOECKMAN, RK ;

BRUZA, KJ .

TETRAHEDRON, 1981, 37 (23) :3997-4006

[2] A CONVERGENT GENERAL SYNTHETIC PROTOCOL FOR CONSTRUCTION OF SPIROCYCLIC KETAL IONOPHORES - AN APPLICATION TO THE TOTAL SYNTHESIS OF (-)-A-23187 (CALCIMYCIN) [J].

BOECKMAN, RK ;

CHARETTE, AB ;

ASBEROM, T ;

JOHNSTON, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7553-7555

[3]

Cardani C., 1966, GAZZ CHIM ITAL, V96, P3

[4] SYNTHETIC ROUTE TO THE TRICARBONYL REGION OF FK-506 [J].

EGBERTSON, M ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :11-12

[5]

IRELAND RE, 1989, TETRAHEDRON LETT, V30, P199

[6] TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].

JONES, TK ;

MILLS, SG ;

REAMER, RA ;

ASKIN, D ;

DESMOND, R ;

VOLANTE, RP ;

SHINKAI, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1157-1159

[7] A SYNTHESIS OF THE C(1)-C(15) SEGMENT OF TSUKUBAENOLIDE (FK 506) [J].

KOCIENSKI, P ;

STOCKS, M ;

DONALD, D ;

COOPER, M ;

MANNERS, A .

TETRAHEDRON LETTERS, 1988, 29 (35) :4481-4484

[8] THE 3,4-DIHYDRO-2H-PYRAN APPROACH TO (+)-MILBEMYCIN-BETA-3 .1. AN ALTERNATIVE SYNTHESIS OF (2S,4S,6R,8R,9S)-2-FORMYLMETHYL-4-(DIMETHYL-TERT-BUTYLSILYLOXY)-8,9-DIMETHYL-1,7-DIOXASPIRO[5.5]UNDECANE [J].

KOCIENSKI, PJ ;

YEATES, C ;

STREET, SDA ;

CAMPBELL, SF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (10) :2183-2187

[9] PREPARATION AND USE OF LITHIATED GLYCALS - VINYLIC DEPROTONATION VERSUS TIN-LITHIUM EXCHANGE FROM 1-TRIBUTYLSTANNYL GLYCALS [J].

LESIMPLE, P ;

BEAU, JM ;

JAURAND, G ;

SINAY, P .

TETRAHEDRON LETTERS, 1986, 27 (51) :6201-6204

[10] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PEDERINE [J].

MATSUDA, F ;

TOMIYOSHI, N ;

YANAGIYA, M ;

MATSUMOTO, T .

TETRAHEDRON, 1988, 44 (23) :7063-7080

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