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

被引：20

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 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)73161-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 6-benzyloxycarbonyl-1-oxa-6-azaspiro[4.5]decane-2-one 7a and 6-benzyloxycarbonyl-1,6-diazaspiro[4.5]decane-2-one 7b from (D,L)-pipecolinic acid is described. The extremely clean decarbonylation of the alpha-substituted amino acid 9d promoted by diphenylphosphorazidate (DPPA) is the key step of our strategy. The total synthesis of (+/-)-delta-coniceine (16) from the enamine ester 10a has been successfully achieved.

引用

页码：4235 / 4238

页数：4

共 20 条

[1] BARTLETT P, 1984, ASYMMETRIC SYNTHESIS, V3
[2] BUTTERY RG, 1983, CHEM IND-LONDON, P478
[3] BYRNE LT, 1992, AUST J CHEM, V45, P1
[4] A STEREOSELECTIVE SYNTHESIS OF (+/-)-H12-HISTRIONICOTOXIN AND RELATED PHOTOAFFINITY-LABELED CONGENERS
EVANS, DA
THOMAS, EW
CHERPECK, RE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3695 - 3700
[5] EVANS DA, 1979, TETRAHEDRON LETT, V40, P411
[6] DESIGN, SYNTHESIS, AND X-RAY CRYSTALLOGRAPHIC ANALYSIS OF 2 NOVEL SPIROLACTAM SYSTEMS AS BETA-TURN MIMICS
GENIN, MJ
GLEASON, WB
JOHNSON, RL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) : 860 - 866
[7] REMOTE DIANIONS .5. SYNTHESIS OF DELTA-CONICEINE
GREEN, DLC
THOMPSON, CM
[J]. TETRAHEDRON LETTERS, 1991, 32 (38) : 5051 - 5054
[8] STEREOSELECTIVITY IN FORMATION OF SPIRO[5.5]UNDECANES BY CATIONIC-PI CYCLIZATION
HARDING, KE
COOPER, JL
PUCKETT, PM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16) : 2834 - 2838
[9] NEW APPROACH TO LYTHRACEAE ALKALOIDS - TOTAL SYNTHESIS OF (+/-)-VERTALINE
HART, DJ
KANAI, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) : 1555 - 1560
[10] NEW SYNTHESIS OF 2-AZETINES AND 1-AZABUTADIENES AND THE USE OF THE LATTER IN DIELS-ALDER REACTIONS - TOTAL SYNTHESIS OF (+/-)-DELTA-CONICEINE
JUNG, ME
CHOI, YM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) : 6729 - 6730

← 1 2 →