Direct conversion of dipropargylic sulfones into (E)- and (Z)-hex-3-ene-1,5-diynes by a modified one-flask Ramberg-Backlund reaction

被引：19

作者：

Cao, XP ^{[1
]}

Chan, TL ^{[1
]}

Chow, HF ^{[1
]}

机构：

[1] CHINESE UNIV HONG KONG,DEPT CHEM,SHA TIN,NT,HONG KONG

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 07期

关键词：

dipropargylic sulfones; enediynes; Ramberg-Backlund reaction;

D O I：

10.1016/0040-4039(95)02345-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)- and (Z)-enediynes 7 are readily synthesized in good yields from a one-pot modified Ramberg-Backlund reaction from dipropargylic sulfones 5.

引用

页码：1049 / 1052

页数：4

共 34 条

[1] CONVENIENT ONE-POT SYNTHESIS OF FUNCTIONALIZED UNSYMMETRICAL (Z)-ENEDIYNES OR (E)-ENEDIYNES FROM (Z)-1,2-DICHLOROETHYLENE OR (E)-1,2-DICHLOROETHYLENE - AN EFFICIENT ROUTE TO (Z,Z,Z) AND (Z,E,Z)-TRIENES [J].

ALAMI, M ;

CROUSSE, B ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1994, 35 (21) :3543-3544

[2] UBER DIE ISOLIERUNG ISOMERER HEXENDIINE AUS LICHTBOGENACETYLEN, DEREN IDENTIFIZIERUNG UND SYNTHESE [J].

BOHMGOSSL, T ;

ROHRSCHNEIDER, L ;

ZIEGENBEIN, W ;

HUNSMANN, W ;

SCHNEIDE.WM .

CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (09) :2504-&

[3] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED 1,3,5-HEXATRIENES FROM DIALLYLIC SULFONES [J].

CAO, XP ;

CHAN, TL ;

CHOW, HF ;

TU, JG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1297-1299

[4] A NEW ONE-FLASK RAMBERG-BACKLUND REACTION [J].

CHAN, TL ;

FONG, S ;

LI, Y ;

MAN, TO ;

POON, CD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) :1771-1772

[5] PI-COMPLEXES INCORPORATING TETRAPHENYLTETRAETHYNYLETHENE [J].

DIEDERICH, F ;

PHILP, D ;

SEILER, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :205-208

[6]

DOI T, 1991, J ORG CHEM, V56, P3465, DOI 10.1021/jo00011a002

[7] TOTAL SYNTHESIS OF CALICHEAMICINONE - NEW ARRANGEMENTS FOR ACTUATION OF THE REDUCTIVE CYCLOAROMATIZATION OF AGLYCON CONGENERS [J].

HASELTINE, JN ;

CABAL, MP ;

MANTLO, NB ;

IWASAWA, N ;

YAMASHITA, DS ;

COLEMAN, RS ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3850-3866

[8] PARA BENZYNE - GENERATION AS AN INTERMEDIATE IN A THERMAL ISOMERIZATION REACTION AND TRAPPING EVIDENCE FOR 1,4-BENZENEDIYL STRUCTURE [J].

JONES, RR ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :660-&

[9] CONVERGENT APPROACH TO INTERMEDIATES USED FOR THE SYNTHESIS OF THE ENEDIYNE STRUCTURE OF THE ESPERAMICINS AND CALICHEAMICINS [J].

KADOW, JF ;

SAULNIER, MG ;

TUN, MM ;

LANGLEY, DR ;

VYAS, DM .

TETRAHEDRON LETTERS, 1989, 30 (27) :3499-3500

[10] SYNTHESIS OF A CALICHEAMICIN DEOXYAGLYCONE MODEL BY AN INTRAMOLECULAR ACETYLIDE CYCLIZATION [J].

KENDE, AS ;

SMITH, CA .

TETRAHEDRON LETTERS, 1988, 29 (34) :4217-4220

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