ENANTIOSELECTIVE RU-MEDIATED SYNTHESIS OF (-)-INDOLIZIDINE-223AB

被引：60

作者：

TABER, DF

DEKER, PB

SILVERBERG, LJ

机构：

[1] Department of Chemistry and Biochemistry, University of Delaware, Newark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 22期

关键词：

D O I：

10.1021/jo00048a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP.Ru*-mediated hydrogenation of the corresponding beta-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80-degrees-C and 50 psig of H-2.

引用

页码：5990 / 5994

页数：5

共 39 条

[1] BENNETT RB, 1989, J AM CHEM SOC, V111, P2581
[2] A SHORT, VERSATILE APPROACH TO POLYHYDROXYLATED PYRROLIDINES UTILIZING A REDUCTIVE ELIMINATION REDUCTIVE AMINATION AS A KEY STEP
BERNOTAS, RC
[J]. TETRAHEDRON LETTERS, 1990, 31 (04) : 469 - 472
[3] BRANDI A, 1989, J ORG CHEM, V54, P1788
[4] A SHORT TOTAL SYNTHESIS OF (+/-)-GEPHYROTOXIN-223AB
BROKA, CA
ENG, KK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) : 5043 - 5045
[5] Daly J. W., 1986, ALKALOIDS CHEM BIOL, V4, P1
[6] REACTIONS OF 1,2-DEHYDROPYRROLIDIN-5-ONE WITH 1,3-DIENES - SYNTHESIS OF DL-GEPHYROTOXIN 223AB
EDWARDS, OE
GREAVES, AM
SY, WW
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (05): : 1163 - 1172
[7] STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B
HOLMES, AB
SMITH, AL
WILLIAMS, SF
HUGHES, LR
LIDERT, Z
SWITHENBANK, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) : 1393 - 1405
[8] INTRAMOLECULAR [4+1] PYRROLINE ANNULATION VIA AZIDE DIENE CYCLO-ADDITIONS .2. FORMAL STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)-PLATYNECINE, (+/-)-HASTANECINE, (+/-)-TURNEFORCIDINE, AND (+/-)-DIHYDROXYHELIOTRIDANE
HUDLICKY, T
SEOANE, G
LOVELACE, TC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) : 2094 - 2099
[9] STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-GEPHYROTOXIN 223AB
IIDA, H
WATANABE, Y
KIBAYASHI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) : 5534 - 5535
[10] HOMOGENEOUS ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES
KITAMURA, M
OHKUMA, T
INOUE, S
SAYO, N
KUMOBAYASHI, H
AKUTAGAWA, S
OHTA, T
TAKAYA, H
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) : 629 - 631

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