TETRAPYRROLES .5. FORMAL SYNTHESES OF THE RING-C,D PYRROMETHENONES OF PHYTOCHROME AND PHYCOCYANIN

被引：22

作者：

JACOBI, PA

DESIMONE, RW

机构：

[1] Hall-Atwater Laboratories, Wesleyan University, Middletown

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 42期

关键词：

PHYTOCHROME; PHYCOCYANIN; PYRROMETHENONES; PD(0)COUPLING; DDQ OXIDATION;

D O I：

10.1016/S0040-4039(00)60942-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formal syntheses of pyrromethenones 2 and 3, potential intermediates for the preparation of phycocyanin (5) and phytochrome (4). respectively. have been accomplished by Pd(o) mediated coupling of iodopyrrole 7 with acetylenic amides of general structure 8a,b, followed by F- catalyzed 5-exo-dig cyclization and DDQ oxidation.

引用

页码：6239 / 6242

页数：4

共 19 条

[1] BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[2] THE REACTION OF THIOIMIDES WITH PHOSPHORUS YLIDES
BISHOP, JE
OCONNELL, JF
RAPOPORT, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) : 5079 - 5091
[3] DIASTEREOSELECTIVE SYNTHESIS OF PHYCOCYANOBILIN CYSTEINE ADDUCTS
BISHOP, JE
NAGY, JO
OCONNELL, JF
RAPOPORT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8024 - 8035
[4] CONVENIENT PREPARATION OF SODIUM AND POTASSIUM PHENYL SELENIDES - REDUCTION OF THE SELENIUM-SELENIUM BOND BY SODIUM HYDRIDE AND POTASSIUM HYDRIDE
DOWD, P
KENNEDY, P
[J]. SYNTHETIC COMMUNICATIONS, 1981, 11 (11) : 935 - 941
[5] NATURAL PRODUCT SYNTHESIS AND VITAMIN-B12
ESCHENMOSER, A
WINTNER, CE
[J]. SCIENCE, 1977, 196 (4297) : 1410 - 1426
[6] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE
EVANS, DA
BRITTON, TC
ELLMAN, JA
[J]. TETRAHEDRON LETTERS, 1987, 28 (49) : 6141 - 6144
[7] SURFACE-ENHANCED RESONANCE RAMAN-SCATTERING SPECTROSCOPY APPLIED TO PHYTOCHROME AND ITS MODEL COMPOUNDS .2. PHYTOCHROME AND PHYCOCYANIN CHROMOPHORES
FARRENS, DL
HOLT, RE
ROSPENDOWSKI, BN
SONG, PS
COTTON, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9162 - 9169
[8] SYNTHESES OF BILE-PIGMENTS .6. TOTAL SYNTHESIS OF (+)(4R,16R)-(18-VINYL)MESOUROBILIN AND (-)(4R,16S)-[18-VINYL]MESOUROBILIN IXALPHA-DIMETHYL ESTERS
GOSSAUER, A
WELLER, JP
[J]. CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (02): : 486 - 501
[9] GOSSAUER A, 1974, LIEBIGS ANN CHEM, P352
[10] PYRROLES AND RELATED COMPOUNDS .17. PORPHYRIN SYNTHESIS THROUGH B-BILENES
JACKSON, AH
KENNER, GW
SMITH, KM
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03): : 502 - &

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