Total synthesis of (+)-crocacin A

被引：17

作者：

Feutrill, JT ^{[1
]}

Rizzacasa, MA ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2003年 / 56卷 / 08期

关键词：

D O I：

10.1071/CH03026

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric total synthesis of the electron-transport inhibitor crocacin A ( 1) is described. The key step involved acylation of the anion derived from dienecarbamate ( 6) with the acid chloride ( 5) to afford the enamide ( 14). Desilylation, oxidation, and N-deprotection gave acid (17), which was coupled with glycine methyl ester to afford (1).

引用

页码：783 / 785

页数：3

共 27 条

[1] SYNTHESIS OF ENAMIDES [J].

BRETTLE, R ;

MOSEDALE, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2185-2195

[2] P-2-NICKEL CATALYST WITH ETHYLENEDIAMINE, A NOVEL SYSTEM FOR HIGHLY STEREOSPECIFIC REDUCTION OF ALKYNES TO CIS-OLEFINS [J].

BROWN, CA ;

AHUJA, VK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (15) :553-554

[3] CATALYTIC-HYDROGENATION .6. REACTION OF SODIUM-BOROHYDRIDE WITH NICKEL SALTS IN ETHANOL SOLUTION - P-2 NICKEL, A HIGHLY CONVENIENT, NEW, SELECTIVE HYDROGENATION CATALYST WITH GREAT SENSITIVITY TO SUBSTRATE STRUCTURE [J].

BROWN, CA ;

AHUJA, VK .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) :2226-2230

[4] REACTION OF SODIUM BOROHYDRIDE WITH NICKEL ACETATE IN ETHANOL SOLUTION-A HIGHLY SELECTIVE NICKEL HYDROGENATION CATALYST [J].

BROWN, HC ;

BROWN, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (07) :1005-&

[5] Total synthesis of (+)-crocacin D [J].

Chakraborty, TK ;

Laxman, P .

TETRAHEDRON LETTERS, 2002, 43 (14) :2645-2648

[6] Total synthesis of (+)-crocacin C [J].

Chakraborty, TK ;

Jayaprakash, S ;

Laxman, P .

TETRAHEDRON, 2001, 57 (46) :9461-9467

[7]

Chakraborty TK, 2001, TETRAHEDRON LETT, V42, P497, DOI 10.1016/S0040-4039(00)02002-5

[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[9] Total synthesis of (+)-crocacin C [J].

Dias, LC ;

de Oliveira, LG .

ORGANIC LETTERS, 2001, 3 (24) :3951-3954

[10] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].

Erickson, KL ;

Beutler, JA ;

Cardellina, JH ;

Boyd, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192

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