The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence:: Synthesis of (+)-paeonilactone B

被引：29

作者：

Edwards, Michael G. ^{[1
]}

Kenworthy, Martin N. ^{[1
]}

Kitson, Russell R. A. ^{[1
]}

Perry, Alexis ^{[1
]}

Scott, Mark S. ^{[1
]}

Whitwood, Adrian C. ^{[1
]}

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

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

tandem reactions; phosphonates; Michael addition; Horner-Wadsworth-Emmons; lactones;

D O I：

10.1002/ejoc.200800558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to alpha-alkylidene-gamma-butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran-2,5-diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)-paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium-catalysed variant proceeding by way of a pi-allyl intermediate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：4769 / 4783

页数：15

共 75 条

[21] Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides [J].

Donald, James R. ;

Edwards, Michael G. ;

Taylor, Richard J. K. .

TETRAHEDRON LETTERS, 2007, 48 (30) :5201-5204

[22] Sesquiterpene Lactones in Arnica montana:: a rapid analytical method and the effects of flower maturity and simulated mechanical harvesting on quality and yield [J].

Douglas, JA ;

Smallfield, BM ;

Burgess, EJ ;

Perry, NB ;

Anderson, RE ;

Douglas, MH ;

Glennie, VLA .

PLANTA MEDICA, 2004, 70 (02) :166-170

[23] The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones:: Synthesis of (+)-paeonilactone B [J].

Edwards, Michael G. ;

Kenworthy, Martin N. ;

Kitson, Russell R. A. ;

Scott, Mark S. ;

Taylor, Richard J. K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1935-1937

[24] Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry [J].

Elford, Tim G. ;

Arimura, Yuichiro ;

Yu, Siu Hong ;

Hall, Dennis G. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1276-1284

[25] SYNTHESIS OF N-(1-CARBOXY-5-AMINOPENTYL)DIPEPTIDES AS INHIBITORS OF ANGIOTENSIN CONVERTING ENZYME [J].

ESCHER, R ;

BUNNING, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :277-278

[26] Catalytic asymmetric intramolecular Michael reaction of aldehydes [J].

Fonseca, MTH ;

List, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3958-3960

[27]

Fraga BM, 1998, NAT PROD REP, V15, P73

[28] SYNTHESIS OF BROMOXONE [J].

GAUTIER, ECL ;

LEWIS, NJ ;

MCKILLOP, A ;

TAYLOR, RJK .

TETRAHEDRON LETTERS, 1994, 35 (47) :8759-8760

[29]

Geissman T A., 1944, Org. React, V2, P94, DOI [10.1002/0471264180.or002.03, DOI 10.1002/0471264180.OR002.03]

[30] ENANTIOSPECIFIC SYNTHESES OF PAEONILACTONE-A, PAEONILACTONE-B, 7S-PAEONIMETABOLIN-I, AND 7R-PAEONIMETABOLIN-I FROM R-(-)-CARVONE [J].

HATAKEYAMA, S ;

KAWAMURA, M ;

SHIMANUKI, E ;

TAKANO, S .

TETRAHEDRON LETTERS, 1992, 33 (03) :333-336

← 1 2 3 4 5 6 7 8 →