LiOH promoted allomerization of pyropheophorbide a.: A convenient synthesis of 132-oxopyropheophorbide a and its unusual enolization

被引：27

作者：

Kozyrev, AN ^{[1
]}

Dougherty, TJ ^{[1
]}

Pandey, RK ^{[1
]}

机构：

[1] Roswell Pk Canc Inst, Dept Radiat Biol, Div Radiat Med, Chem Sect, Buffalo, NY 14263 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 04期

关键词：

D O I：

10.1039/a707805f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of pyropheophorbide a with aqueous LiOH-THF gave the corresponding enolate, which on in situ oxidation produced the corresponding 13(2)-oxo derivative in 79% yield; prolonged autoxidation gave purpurin-18 and purpurin-5 as major products and a mechanism for the formation of 12-formyl derivative from 13(2)-oxopyropheophorbide a under unusual enolization is discussed; the electronic absorption spectroscopy data of the enolic intermediates showed a considerable perturbation in the pi-systems of the macrocycle.

引用

页码：481 / 482

页数：2

共 11 条

[1] Studies in the chlorophyll series. I. The thermal decomposition of the magnesium-free compounds
Conant, JB
Hyde, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1929, 51 : 3668 - 3674
[2] Hynninen P. H., 1991, CHLOROPHYLLS, P145
[3] Syntheses of stable bacteriochlorophyll-a derivatives as potential photosensitizers for photodynamic therapy
Kozyrev, AN
Zheng, G
Zhu, CF
Dougherty, TJ
Smith, KM
Pandey, RK
[J]. TETRAHEDRON LETTERS, 1996, 37 (36) : 6431 - 6434
[4] Syntheses of emeraldin and purpurin-18 analogs as target-specific photosensitizers for photodynamic therapy
Kozyrev, AN
Zheng, G
Lazarou, E
Dougherty, TJ
Smith, KM
Pandey, RK
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3335 - 3338
[5] KOZYREV AN, UNPUB
[6] MA L, 1996, J ORG CHEM, V61, P250
[7] SMITH KM, 1975, GEN FEATURES STRUCTU
[8] STRUCTURAL COMPARISON OF NICKEL, VANADYL, COPPER, AND FREE BASE PORPHYRINS FROM OULAD ABDOUN OIL-SHALE (MAASTRICHTIAN, MOROCCO)
VERNEMISMER, J
OCAMPO, R
BAUDER, C
CALLOT, HJ
ALBRECHT, P
[J]. ENERGY & FUELS, 1990, 4 (06) : 639 - 643
[9] MONOMERIC CHLOROPHYLL A-ENOL - EVIDENCE FOR ITS POSSIBLE ROLE AS THE PRIMARY ELECTRON-DONOR IN PHOTOSYSTEM-I OF PLANT PHOTOSYNTHESIS
WASIELEWSKI, MR
NORRIS, JR
SHIPMAN, LL
LIN, CP
SVEC, WA
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (05): : 2957 - 2961
[10] Willstatter Richard., 1913, Untersuchungen uber chlorophyll

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