Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach

被引：45

作者：

Burns, Alan R. ^{[1
]}

McAllister, Graeme D. ^{[1
]}

Shanahan, Stephen E. ^{[2
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] GlaxoSmithKline, Chem Dev, Old Powder Mills, Tonbridge TN11 9AN, Kent, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 32期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

dictyosphaeric acid; metathesis; Michael addition; tandem reactions; total synthesis; EFFICIENT;

D O I：

10.1002/anie.201002416

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) The acid test? The synthetic route to the title compound features a Z-selective ring-closing metathesis reaction and an E-selective tandem intramolecular Michael addition/alkene migration sequence as the key transformations. The stereochemical configuration of the product was reassigned based on NMR studies. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5574 / 5577

页数：4

共 16 条

[1] A convergent synthesis of the tricyclic core of the dictyosphaeric acids [J].

Barfoot, Christopher W. ;

Burns, Alan R. ;

Edwards, Michael G. ;

Kenworthy, Martin N. ;

Ahmed, Mahmood ;

Shanahan, Stephen E. ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2008, 10 (02) :353-356

[2] Approaches to the synthesis of (+)- and (-)-epibatidine [J].

Barros, MT ;

Maycock, CD ;

Ventura, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (02) :166-173

[3] Dictyosphaeric acids A and B:: New decalactones from an undescribed Penicillium sp obtained from the alga Dictyosphaeria versluyii [J].

Bugni, TS ;

Janso, JE ;

Williamson, RT ;

Feng, XD ;

Bernan, VS ;

Greenstein, M ;

Carter, GT ;

Maiese, WM ;

Ireland, CM .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1396-1399

[4] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2007, 9 (26) :5397-5400

[5]

Drew MGB, 2002, EUR J ORG CHEM, V2002, P3589

[6]

Dupau P, 2002, ADV SYNTH CATAL, V344, P421, DOI 10.1002/1615-4169(200206)344:3/4<421::AID-ADSC421>3.0.CO

[7]

2-F

[8] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[9] Colletofragarones A1 and A2, novel germination self-inhibitors from the fungus Colletotrichum fragariae [J].

Inoue, M ;

Takenaka, H ;

Tsurushima, T ;

Miyagawa, H ;

Ueno, T .

TETRAHEDRON LETTERS, 1996, 37 (32) :5731-5734

[10] SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY PALLADIUM(II)-CATALYZED DEHYDROSILYLATION OF SILYL ENOL ETHERS [J].

ITO, Y ;

HIRAO, T ;

SAEGUSA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :1011-1013

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