TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID POSSESSING AN 11-MEMBERED RETRONECINE DILACTONE

被引：28

作者：

NIWA, H

OGAWA, T

OKAMOTO, O

YAMADA, K

机构：

[1] Department of Chemistry, Faculty of Science, Nagoya University, Chikusa, Nagoya

来源：

TETRAHEDRON | 1992年 / 48卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(01)88350-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the natural enantiomer of monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids having an 11-membered retronecine dilactone was achieved through regioselective coupling of (+)-retronecine (3) and the optically active protected necic acid 8, the latter being prepared enantioselectively from the meso-diester 11.

引用

页码：10531 / 10548

页数：18

共 54 条

[21] TOTAL SYNTHESIS OF A MACROCYCLIC PYRROLIZIDINE ALKALOID, (+/-)-INTEGERRIMINE, UTILIZING AN ACTIVABLE PROTECTING GROUP
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[23] A TIN-MEDIATED ONE-STEP SYNTHESIS OF (+)-DICROTALINE, AN 11-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID
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[24] TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIMINE, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE .2. ENANTIOSELECTIVE SYNTHESIS OF (+)-RETRONECINE
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[25] TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID HAVING AN 11-MEMBERED DILACTONE
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[26] TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIMINE, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE
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[27] AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF THE (-)-N-(ETHOXYCARBONYL)METHYL GEISSMAN-WAISS LACTONE - A PRACTICAL SYNTHETIC ROUTE TO (+)-RETRONECINE
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[28] TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIME, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE .1. ENANTIOSELECTIVE SYNTHESIS OF THE PROTECTED (+/-)-INTEGERRINECIC ACID
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[29] ENANTIOSELECTIVE SYNTHESIS OF S-1452, AN ORALLY ACTIVE POTENT THROMBOXANE-A2 RECEPTOR ANTAGONIST
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2122 - 2127
[30] HIGHLY EFFECTIVE AND PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF HALF-ESTERS OF BICYCLO[2.2.1]HEPTANEDICARBOXYLIC ACID
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