AMINO-ACIDS AS PRECURSORS TO INDOLIZIDINE ALKALOIDS - DPPA-PROMOTED DECARBONYLATION OF A BICYCLIC AMINO-ACID - AN EASY ENTRY TO HYDROXYLATED INDOLIZIDINES

被引：24

作者：

MARTINLOPEZ, MJ ^{[1
]}

BERMEJOGONZALEZ, F ^{[1
]}

机构：

[1] UNIV SALAMANCA,FAC QUIM,DEPT QUIM ORGAN,E-37008 SALAMANCA,SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)78513-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 8,8a-trans-8-hydroxr-indolizidine 12 from (D,L)-pipecolinic acid by two alternative routes is described. The stereospecific decarbonylation of the bicyclic carboxyamide 9 promoted by diphenylphosphorazidate (DPPA) is the key step of our strategy. The bicyclic enamide 10 is described as a valuable intermediate in the synthesis of hydroxulated indolizidines.

引用

页码：8843 / 8846

页数：4

共 13 条

[1]

[Anonymous], 1987, ALKALOIDS CHEM BIOL

[2] SYNTHETIC APPROACHES TO STEREOISOMERS AND ANALOGS OF CASTANOSPERMINE [J].

BURGESS, K ;

HENDERSON, I .

TETRAHEDRON, 1992, 48 (20) :4045-4066

[3] SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE [J].

CORDERO, FM ;

CICCHI, S ;

GOTI, A ;

BRANDI, A .

TETRAHEDRON LETTERS, 1994, 35 (06) :949-952

[4]

FLITSCH W, 1987, LIEBIGS ANN CHEM, P649

[5]

HOWARD AS, 1986, ALKALOIDS, V28, P183

[6]

KIBAYASHI C, 1991, TETRAHEDRON LETT, V32, P4147

[7] ENANTIOSPECIFIC SYNTHESIS OF FUNCTIONALIZED INDOLIZIDINES - SYNTHESIS OF (8S,8AR)-6,7-DEHYDRO-8-HYDROXYINDOLIZIDINE [J].

KOSKINEN, AMP ;

PAUL, JM .

TETRAHEDRON LETTERS, 1992, 33 (45) :6853-6856

[8] FRAGMENTATION AND AN NESMEYANOVS CONCEPT OF SIGMA-CONJUGATION [J].

MAKSIMOV, VI .

TETRAHEDRON, 1965, 21 (04) :687-&

[9] DPPA-PROMOTED DECARBONYLATION OF A N-CBZ-(D,L)-PIPECOLINIC ACID-DERIVATIVE - AN EASY ENTRY TO [4.5]SPIROLACTAMS AND [4.5]SPIROLACTONES - TOTAL SYNTHESIS OF (+/-)-DELTA-CONICEINE [J].

MARTINLOPEZ, MJ ;

BERMEJOGONZALEZ, F .

TETRAHEDRON LETTERS, 1994, 35 (24) :4235-4238

[10]

MICHAEL JP, 1990, NAT PROD REP, P485

← 1 2 →