Total synthesis of (-)-reserpine using the chiron approach

被引：52

作者：

Hanessian, S

Pan, JW

Carnell, A

Bouchard, H

Lesage, L

机构：

[1] Department of Chemistry, Université de Montréal, Station Centreville, Montréal, Que. H3C 3J7

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 03期

关键词：

D O I：

10.1021/jo961713w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereocontrolled synthesis of ring D/E precursor to reserpine has been developed starting from (-)-quinic acid as a chiral template. The total synthesis of(-)-reserpine is described through the cyclization of an immonium lactam intermediate.

引用

页码：465 / 473

页数：9

共 84 条

[1] Albertini E, 1996, SYNLETT, P29
[2] ATTAURRAHMAN, 1994, STUDIES NATURAL PROD, V1
[3] SYMMETRY-DRIVEN SYNTHESIS OF INDOLE ALKALOIDS - ASYMMETRIC TOTAL SYNTHESES OF (+)-YOHIMBINE, (-)-YOHIMBONE, (-)-YOHIMBANE, AND (+)-ALLOYOHIMBANE
AUBE, J
GHOSH, S
TANOL, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 9009 - 9018
[4] BARROS MT, 1994, TETRAHEDRON LETT, V23, P3999
[5] DIRECT BUTYROLACTONE PRODUCTION USING TIN HYDRIDE
BELLETIRE, JL
MAHMOODI, NO
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4363 - 4366
[6] BLASKO G, 1986, LIEBIGS ANN CHEM, P655
[7] SYNTHESIS OF DERIVATIVES OF 2,6-DIDEOXY-2,2-DIFLUORO-3-O-METHYL-L-ARABINOPYRANOSE (2,2-DIFLUOROOLEANDROSE)
BLIARD, C
HERCZEGH, P
OLESKER, A
LUKACS, G
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (01) : 103 - 113
[8] Brown H.C., 1972, BORANES ORGANIC CHEM
[9] RAUWOLFIA ALKALOID SYNTHESIS APPROACH EMPLOYING THE ZWITTERIONIC AMINO-CLAISEN REARRANGEMENT - IMPROVEMENTS IN THE EFFICIENCY FOR YOHIMBANE RING CONSTRUCTION AND UNAMBIGUOUS DE-RING-FUSION STEREOCHEMICAL ASSIGNMENTS
CHAO, S
KUNNG, FA
GU, JM
AMMON, HL
MARIANO, PS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) : 2708 - 2711
[10] Corey E.J., 1989, The Logic of Chemical Synthesis

← 1 2 3 4 5 6 7 8 9 →