A concise asymmetric synthesis of the ADE fragment of nakadomarin

被引：72

作者：

Ahrendt, KA ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 24期

关键词：

D O I：

10.1021/ol048126e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ADE fragment of nakadomarin A has been synthesized in nine linear steps from commercial material. The key transformation is an asymmetric azomethine ylide [1,3]-dipolar cycloaddition to establish the AD-spirocyclic system containing three of the four stereocenters of the natural product.

引用

页码：4539 / 4541

页数：3

共 28 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2] Electronic structure description of the μ4-sulfide bridged tetranuclear Cuz center in N2O reductase [J].

Chen, P ;

George, SD ;

Cabrito, I ;

Antholine, WE ;

Moura, JJG ;

Moura, I ;

Hedman, B ;

Hodgson, KO ;

Solomon, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :744-745

[3] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

[4] Large scale synthesis of cyclodiphospho-d-glycerate [J].

Earle, MJ ;

AbdurRashid, A ;

Priestley, ND .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5697-5700

[5]

Fürstner A, 2001, CHEM-EUR J, V7, P4811, DOI 10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO

[6]

2-P

[7]

GAREGG PJ, 1979, SYNTHESIS-STUTTGART, P469

[8]

Gothelf AS, 2002, ANGEW CHEM INT EDIT, V41, P4236, DOI 10.1002/1521-3773(20021115)41:22<4236::AID-ANIE4236>3.0.CO

[9]

2-W

[10] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

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