An Ireland-Claisen Rearrangement/Lactonisation Cascade as a Key Step in Studies Towards the Synthesis of (-)-Euonyminol

被引：6

作者：

Webber, Matthew J. ^{[1
]}

Weston, Matthew ^{[2
]}

Grainger, Damian M. ^{[1
,2
]}

Lloyd, Stacy ^{[1
]}

Warren, Sarah A. ^{[1
]}

Powell, Lyn ^{[3
]}

Alanine, Alexander ^{[4
]}

Stonehouse, Jeffrey P. ^{[5
]}

Frampton, Christopher S. ^{[6
]}

White, Andrew J. P. ^{[1
]}

Spivey, Alan C. ^{[1
,2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[3] AstraZeneca Proc Res & Dev, Macclesfield SK10 2NA, Cheshire, England

[4] F Hoffmann La Roche Ltd, Pharma Res & Early Dev, PRED, CH-4070 Basel, Switzerland

[5] AstraZeneca R&D, Dept Med Chem, Loughborough LE11 5RH, Leics, England

[6] Pharmorphix Solid State Serv, Sigma Aldrich Grp, Cambridge CB4 0WE, England

来源：

SYNLETT | 2011年 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

Ireland-Claisen; Celastraceae; bromination; euonyminol; sesquiterpene; CELASTRACEAE SESQUITERPENOIDS; STEREOSELECTIVE-SYNTHESIS; TRIPTERYGIUM-HYPOGLAUCUM; HYDROXYLATION; WILFORDII; ALKALOIDS; LACTONES; ESTERS;

D O I：

10.1055/s-0031-1289543

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Progress towards the asymmetric total synthesis of (-)-euonyminol is described with the focus on the installation of the oxygenation pattern on the lower rim of the molecule. An Ireland-Claisen rearrangement/lactonisation cascade has been developed and studies towards further elaboration have uncovered an intriguing tunable diastereoselective alpha-bromination of the resulting gamma-lactone.

引用

页码：2693 / 2696

页数：4

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