Regio- and diastereoselective synthesis of lissoclinolide analogues by Lewis acid catalyzed cyclization of the first 1,5-bis(trimethylsilyloxy)-1,3,5-hexatrienes with oxalyl chloride

被引：22

作者：

Langer, P ^{[1
]}

Freifeld, I ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

来源：

SYNLETT | 2001年 / 04期

关键词：

butenolides; cyclizations; oxalic acid; regioselectivity; silyl enol ethers;

D O I：

10.1055/s-2001-12327

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid catalyzed cyclization of 1,5-bis(trimethylsilyloxy)-1,3,5-hexatrienes with oxalyl chloride resulted in formation of polyunsaturated butenolides.

引用

页码：523 / 525

页数：3

共 38 条

[1] RULES FOR RING-CLOSURE - STEREOELECTRONIC CONTROL IN ENDOCYCLIC ALKYLATION OF KETONE ENOLATES [J].

BALDWIN, JE ;

KRUSE, LI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (07) :233-235

[2] SYNTHESIS AND REACTIONS OF DERIVATIVES OF 1,7-DIOXASPIRO[5.5]UNDEC-2-EN-4-ONE [J].

BARRETT, AGM ;

CARR, RAE ;

FINCH, MAW ;

FLORENT, JC ;

RICHARDSON, G ;

WALSHE, NDA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4254-4260

[3]

CAMBILLAU C, 1976, TETRAHEDRON LETT, P281

[4]

CHAN TH, 1979, J CHEM SOC CHEM COMM, P578, DOI 10.1039/c39790000578

[5] CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].

CHAN, TH ;

BROWNBRIDGE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538

[6] CHEMISTRY OF 1,3,5-TRIS(TRIMETHYLSILOXY)-1-METHOXYHEXA-1,3,5-TRIENE, A BETA-TRICARBONYL TRIANION EQUIVALENT [J].

CHAN, TH ;

STOSSEL, D .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2423-2428

[7] STRUCTURE OF TETRENOLIN - A NEW ANTIBIOTIC SUBSTANCE [J].

GALLO, GG ;

CORONELLI, C ;

VIGEVANI, A ;

LANCINI, GC .

TETRAHEDRON, 1969, 25 (23) :5677-+

[8]

Gorth FC, 1998, EUR J ORG CHEM, V1998, P1055

[9]

Görth FC, 1999, SYNTHESIS-STUTTGART, P1520

[10] HIGHLY DIASTEREOSELECTIVE TITANIUM TETRACHLORIDE-MEDIATED ALDOL CONDENSATION OF THE BISTRIMETHYLSILYL ENOL ETHER OF ACETOACETIC ESTER WITH 2-BENZYLOXYHEXANAL - A SYNTHESIS OF (-)-PESTALOTIN [J].

HAGIWARA, H ;

KIMURA, K ;

UDA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (11) :860-861

← 1 2 3 4 →