ASYMMETRIC-SYNTHESIS OF PIPERIDINE ALKALOIDS UTILIZING DIASTEREOSELECTIVE REACTION OF 1,3-OXAZOLIDINE WITH GRIGNARD-REAGENTS

被引：30

作者：

HIGASHIYAMA, K

NAKAHATA, K

TAKAHASHI, H

机构：

[1] Faculty of Pharmaceutical Science, Hoshi University, Shinagawa-ku, Tokyo, 142

来源：

HETEROCYCLES | 1992年 / 33卷 / 01期

关键词：

D O I：

10.3987/COM-91-S1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method of synthesizing enantiomerically pure piperidine alkaloids, (R)-(-)-coniine and (2R, 6S)-(-)-dihydropinidine, has been explored by employing the highly diastereoselective reaction of a 1,3-oxazolidine with Griganard reagents.

引用

页码：17 / 20

页数：4

共 6 条

[1] AKETA K, 1976, CHEM PHARM BULL, V24, P621
[2] CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENTS - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALKALOIDS - THE ENANTIOSPECIFIC SYNTHESIS OF (+)-CONIINE AND (-)-CONIINE AND DIHYDROPINIDINE
GUERRIER, L
ROYER, J
GRIERSON, DS
HUSSON, HP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) : 7754 - 7755
[3] APPROACH TO NATURAL 2-ALKYL-6-METHYLPIPERIDINES VIA N-ACYLLACTAM REARRANGEMENT
HILL, RK
YURI, T
[J]. TETRAHEDRON, 1977, 33 (13) : 1569 - 1571
[4] GAMMA-CHLOROBUTYRALDEHYDE AND ITS DIETHYL ACETAL
LOFTFIELD, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) : 1365 - 1366
[5] ASYMMETRIC INDUCTION BY CHIRAL HETEROCYCLIC-COMPOUNDS - REACTION OF CHIRAL N-METHYL-4-PHENYL-1,3-OXAZOLIDINES WITH ORGANOMETALLIC REAGENTS
TAKAHASHI, H
NIWA, H
HIGASHIYAMA, K
[J]. HETEROCYCLES, 1988, 27 (09) : 2099 - 2102
[6] TAKAHASHI H, 1990, CHEM PHARM BULL, V38, P2429

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