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

共 50 条

[41] STEREOCONTROLLED, 2-DIRECTIONAL, CHAIN SYNTHESIS USING THE BORON ALDOL REACTION AND DOUBLE IRELAND-CLAISEN REARRANGEMENT
PATERSON, I
HULME, AN
WALLACE, DJ
TETRAHEDRON LETTERS, 1991, 32 (51) : 7601 - 7604
[42] Development of the Ireland-Claisen Rearrangement of Alkoxy- and Aryloxy-Substituted Allyl Glycinates
Tellam, James P.
Carbery, David R.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22): : 7809 - 7821
[43] Stereoselective construction of an anti-β-alkoxy ether by Ireland-Claisen rearrangement for medium-ring ether synthesis
Fujiwara, Kenshu
Kawamura, Natsumi
Kawai, Hidetoshi
Suzuki, Takanori
TETRAHEDRON LETTERS, 2009, 50 (11) : 1236 - 1239
[44] CONSTRUCTION OF LARGE CARBOCYCLIC RINGS BY IRELAND-CLAISEN REARRANGEMENT OF O-SILYLATED LACTONE ENOLATES - SYNTHESIS OF (+/-)-MUSCONE
BRUNNER, RK
BORSCHBERG, HJ
HELVETICA CHIMICA ACTA, 1983, 66 (08) : 2608 - 2614
[45] Ireland-Claisen Rearrangement of 6-Methylene-1,4-oxazepan-2-ones
Smits, Gints
Kinens, Artis
Zemribo, Ronalds
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (30) : 6701 - 6709
[46] Application of chelation controlled Ireland-Claisen rearrangement in the total syntheses of Barmumycin and Limazepine E
Smits, Gints
Zemribo, Ronalds
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[47] A novel and expedient synthesis of optically active fluoroalkylated amino acids via palladium-catalyzed allylic rearrangement and Ireland-Claisen rearrangement
Konno, T
Daitoh, T
Ishihara, T
Yamanaka, H
TETRAHEDRON-ASYMMETRY, 2001, 12 (19) : 2743 - 2748
[48] Synthesis of a constitutional isomer of nerol by consecutive Ireland-Claisen and Cope rearrangements
Kraft, P
Eichenberger, W
Fráter, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (11) : 2781 - 2785
[49] Synthesis of indolizidines from L-pyroglutamic acid using the Ireland-Claisen rearrangement and ring-closing metathesis
Essayan, Daniel
Cannon, Jeff
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[50] Ireland-Claisen rearrangement for the stereoselective formation of the C2-C3 bond in taxanes
Magnus, P
Westwood, N
TETRAHEDRON LETTERS, 1999, 40 (25) : 4659 - 4662

← 1 2 3 4 5 →