Total synthesis of (+)-crocacin D

被引：31

作者：

Feutrill, JT ^{[1
]}

Lilly, MJ ^{[1
]}

Rizzacasa, MA ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol017092x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric synthesis of (+)-crocacin D (4) is described. The key steps in the sequence are the stereoselective assembly of the stereotetrad via a substrate-controlled aldol reaction and anti-selective reduction, formation of the (EE)-diene by a Stille cross-coupling between the stannane 8 and vinyl iodide 9, and the acylation of (Z)-enecarbamate 6 with the acid chloride derived from polyketide fragment 16 which introduced the (Z)-enamide functionality.

引用

页码：525 / 527

页数：3

共 34 条

[1] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1934-1939

[2]

[Anonymous], 1997, ORGANIC REACTIONS

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

Chakraborty, TK ;

Jayaprakash, S ;

Laxman, P .

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

[4]

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

[5] APPLICATION OF THE IBUKA-YAMAMOTO REACTION TO A PROBLEM IN STEREOCHEMICAL COMMUNICATION - A STRATEGY FOR THE STEREOSPECIFIC SYNTHESIS AND STABILIZATION OF THE TRIENE SUBSTRUCTURE OF RAPAMYCIN THROUGH SULFONE SUBSTITUTION [J].

CHEN, SH ;

HORVATH, RF ;

JOGLAR, J ;

FISHER, MJ ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5834-5845

[6] Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B [J].

Cuzzupe, AN ;

Hutton, CA ;

Lilly, MJ ;

Mann, RK ;

McRae, KJ ;

Zammit, SC ;

Rizzacasa, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2382-2393

[7] 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

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

Dias, LC ;

de Oliveira, LG .

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

[9] A comprehensive survey of Stille-type Csp2-Csp2 single bond forming processes in the synthesis of retinoic acid and analogs [J].

Domínguez, B ;

Iglesias, B ;

de Lera, AR .

TETRAHEDRON, 1999, 55 (52) :15071-15098

[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

← 1 2 3 4 →