Total synthesis of natural (-)-codonopsinine employing stereoselective reduction of quaternary alpha-hydroxypyrrolidine

被引：77

作者：

Yoda, H

Nakajima, T

Takabe, K

机构：

[1] Department of Molecular Science, Faculty of Engineering, Shizuoka University

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 31期

关键词：

D O I：

10.1016/0040-4039(96)01042-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient process is described for the total synthesis of a dihydroxypyrrolidine alkaloid, (-)-codonopsinine in 33% overall yield. The synthetic strategy is based on the stereoselective reduction of an alpha-hydroxypyrrolidine intermediate, elaborated through asymmetric deoxygenation of a homochiral quaternary alpha-hydroxylactam. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5531 / 5534

页数：4

共 15 条

[1] PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE REDUCTION OF DIPROTECTED ALPHA,ALPHA-BIS(HYDROXYMETHYL)KETONES DERIVED FROM THYM-ASTERISK, USING THE DIBALH MGBR2 SYSTEM
GUANTI, G
BANFI, L
RIVA, R
ZANNETTI, MT
[J]. TETRAHEDRON LETTERS, 1993, 34 (34) : 5483 - 5486
[2] TOTAL SYNTHESIS OF (+)-CODONOPSININE AND ITS STEREOISOMERS - STEREOCHEMICAL ASSIGNMENT OF NATURAL (-)-CODONOPSININE
IIDA, H
YAMAZAKI, N
KIBAYASHI, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) : 1956 - 1962
[3] STEREOCHEMICAL REVISION AND ABSOLUTE-CONFIGURATION OF CODONOPSININE
IIDA, H
YAMAZAKI, N
KIBAYASHI, C
NAGASE, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (44) : 5393 - 5396
[4] Khanov M. T., 1971, FARMAKOL ALKALOIDOV, P210
[5] MATKHALIKOVA S F, 1969, KHIM PRIR SOEDIN (TASHK), V5, P30
[6] Matkhalikova S. F., 1969, KHIM PRIR SOEDIN+, V5, P607
[7] Matkhalikova S F, 1969, KHIM PRIR SOEDIN+, V5, P606
[8] MATKHALIKOVA SF, 1971, KHIM PRIR SOEDIN, V7, P210
[9] STEREOSELECTIVE REDUCTION OF 2-METHYL-3-OXO ESTERS (OR AMIDES) WITH SODIUM-BOROHYDRIDE CATALYZED BY MANGANESE(II) CHLORIDE OR TETRABUTYLAMMONIUM BOROHYDRIDE - A PRACTICAL PREPARATION OF ERYTHRO AND THREO-3-HYDROXY-2-METHYL ESTERS (OR AMIDES)
TANIGUCHI, M
FUJII, H
OSHIMA, K
UTIMOTO, K
[J]. TETRAHEDRON, 1993, 49 (48) : 11169 - 11182
[10] DECARBOXYLATIVE CYCLIZATION OF ALLYLIC CYCLIC CARBAMATES - APPLICATIONS TO THE TOTAL SYNTHESIS OF (-)-CODONOPSINE
WANG, CLJ
CALABRESE, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) : 4341 - 4343

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