NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .92. A STEREOSELECTIVE SYNTHESIS OF TILIVALLINE AND ITS ANALOGS

被引：46

作者：

MORI, S ^{[1
]}

OHNO, T ^{[1
]}

HARADA, H ^{[1
]}

AOYAMA, T ^{[1
]}

SHIOIRI, T ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,TANABE DORI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 27期

关键词：

TILIVALLINE; PYRROLO[2,1-C][1,4]BENZODIAZEPIN-5-ONE; MANNICH TYPE CYCLIZATION; DIPHENYL PHOSPHORAZIDATE; DIETHYL PHOSPHOROCYANIDATE;

D O I：

10.1016/S0040-4020(01)80968-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tilivalline (1a), a metabolite from Klebsiella pneumoniae var. oxytoca, and its derivatives 1 have been efficiently and stereoselectively synthesized from diphenyl phosphorazidate, the 2-oxazoline 2, the L-proline derivatives 5, and indole; the key step is a Mannich type intramolecular cyclization accompanied with completely stereoselective introduction of indole. Furthermore, 11-substituted 5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-ones (16) have been also synthesized from the acetal amide 9a and various nucleophiles by the use of this new Mannich type cyclization.

引用

页码：5051 / 5070

页数：20

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