Extension of the eschenmoser sulfide contraction iminoester cyclization method to the synthesis of tolyporphin chromophore

被引：39

作者：

Minehan, TG ^{[1
]}

Kishi, Y ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM & CHEM BIOL,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01601-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tolyporphin chromophore 2 has been synthesized by performing a double-retroaldol/oxidation sequence on an octahydroporphyrin precursor 28 prepared by using the Eschenmoser sulfide-contraction/iminoester-condensation method. (C) 1997 Elsevier Science Ltd.

引用

页码：6811 / 6814

页数：4

共 14 条

[1] Synthesis of stipiamide and a new multidrug resistance reversal agent, 6,7-dehydrostipiamide [J].

Andrus, MB ;

Lepore, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2327-2328

[2]

COREY EJ, 1973, TETRAHEDRON LETT, P4499

[3] ROADS TO CORRINS [J].

ESCHENMOSER, A .

QUARTERLY REVIEWS, 1970, 24 (03) :366-+

[4]

GHOSH AK, 1996, Z ANGEW CHEM INT ED, V35, P74

[5]

GOTSCHI E, 1973, ANGEW CHEM INT EDIT, V11, P910

[6] CORPHIN A CORRINOID-PORPHINOID LIGAND SYSTEM [J].

JOHNSON, AP ;

WEHRLI, P ;

FLETCHER, R ;

ESCHENMO.A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (08) :623-&

[7]

MULLER PM, 1973, ANGEW CHEM INT EDIT, V11, P914

[8] Pinacol-pinacolone rearrangements in vic-dihydroxychlorins and bacteriochlorins: Effect of substituents at the peripheral positions [J].

Pandey, RK ;

Isaac, M ;

MacDonald, I ;

Medforth, CJ ;

Senge, MO ;

Dougherty, TJ ;

Smith, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1463-1472

[9]

PASTAN I, 1993, ANNU REV BIOCHEM, V62, P385

[10] TOLYPORPHIN, A NOVEL MULTIDRUG RESISTANCE REVERSING AGENT FROM THE BLUE-GREEN-ALGA TOLYPOTHRIX-NODOSA [J].

PRINSEP, MR ;

CAPLAN, FR ;

MOORE, RE ;

PATTERSON, GML ;

SMITH, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :385-387

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