Syntheses of oxygen analogues of sulfhemes-A and -C

被引：15

作者：

Iakovides, P ^{[1
]}

Smith, KM ^{[1
]}

机构：

[1] UNIV CALIF DAVIS, DEPT CHEM, DAVIS, CA 95616 USA

来源：

TETRAHEDRON | 1996年 / 52卷 / 04期

基金：

美国国家卫生研究院;

关键词：

porphyrin epoxides; porphyrin photo-oxygenation; Mitsunobu reaction; OXIDATION-REDUCTION CONDENSATION; DISSIMILATORY NITRITE REDUCTASE; PORPHYRIN DIMERS; PROSTHETIC GROUP; VIC-DIHYDROXYCHLORINS; PHOTODYNAMIC THERAPY; PROTOPORPHYRIN-IX; MODEL COMPOUNDS; ETHER LINKAGES; VINYL GROUPS;

D O I：

10.1016/0040-4020(95)00953-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of metal-free oxygen analogues of the sulfhemes-A and -C from protoporphyrin-IX dimethyl ester 1 are presented. Oxasulfporphyrin-C dimethyl ester 5 is obtained by intramolecular displacement of a primary tosylate by a tertiary hydroxyl in an appropriately constructed precursor 18, or by surface-catalyzed rearrangement of the epoxide-bearing oxasulfporphyrin-A dimethyl ester 23. Compound 23 is in turn prepared by Mitsunobu type internal;dehydration of the precursor 12. The methodology is then successfully extended to more symmetric porphyrin systems. Compounds 23, 25, 46, and 61/62 are the first porphyrin epoxides to be synthesized.

引用

页码：1123 / 1148

页数：26

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