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

被引：66

作者：

Edwards, Michael G. ^{[1
]}

Kenworthy, Martin N. ^{[1
]}

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

Scott, Mark S. ^{[1
]}

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

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

alpha-methylene lactones; Michael addition; olefination; phosphonates; tandem reactions;

D O I：

10.1002/anie.200705329

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/ Horner-Wadsworth-Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ- butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1935 / 1937

页数：3

共 33 条

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

Fonseca, MTH ;

List, B .

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

[12] 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

[13] TOTAL SYNTHESES OF (+)-PAEONILACTONE-B AND (-)-PAEONISUFFRONE [J].

HATAKEYAMA, S ;

KAWAMURA, M ;

MUKUGI, Y ;

IRIE, H .

TETRAHEDRON LETTERS, 1995, 36 (02) :267-268

[14] PAEONILACTONE-A, PAEONILACTONE-B, AND PAEONILACTONE-C, NEW MONOTERPENOIDS FROM PAEONY ROOT [J].

HAYASHI, T ;

SHINBO, T ;

SHIMIZU, M ;

ARISAWA, M ;

MORITA, N ;

KIMURA, M ;

MATSUDA, S ;

KIKUCHI, T .

TETRAHEDRON LETTERS, 1985, 26 (31) :3699-3702

[15] Novel synthesis, cytotoxic evaluation, and structure-activity relationship studies of a series of α-alkylidene-γ-lactones and lactams [J].

Janecki, T ;

Blaszczyk, E ;

Studzian, K ;

Janecka, A ;

Krajewska, U ;

Rózalski, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) :3516-3521

[16]

KANG, 2002, ANGEW CHEM, V114, P1654

[17]

Kang SK, 2002, ANGEW CHEM INT EDIT, V41, P1584, DOI 10.1002/1521-3773(20020503)41:9<1584::AID-ANIE1584>3.0.CO

[18]

2-Y

[19] Intramolecular cyclization of (2-functionalized allyl)trimethylsilane with acid chloride.: Synthesis of two guaianolide-type α-methylene γ-lactones [J].

Kuroda, C ;

Kobayashi, K ;

Koito, A ;

Anzai, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (10) :1947-1961

[20]

Little R. D., 1995, ORG REACTIONS, V47, P315, DOI 10.1002/0471264180.or047.02

← 1 2 3 4 →