A NOVEL SYNTHESIS OF FURANS BY BASE-CATALYZED ISOMERIZATION OF ALKYNYLOXIRANES

被引：26

作者：

MARSHALL, JA

DUBAY, WJ

机构：

[1] Department of Chemistry, The University of South Carolina, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 05期

关键词：

D O I：

10.1021/jo00005a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alkynloxiranes 3 with KO-t-Bu in t-BuOH causes isomerization to the furans 4. A pathway involving a cumulene alkoxide is proposed.

引用

页码：1685 / 1687

页数：3

共 10 条

[1] PSEUDOPTEROLIDE, AN IRREGULAR DITERPENOID WITH UNUSUAL CYTO-TOXIC PROPERTIES FROM THE CARIBBEAN SEA WHIP PSEUDOPTEROGORGIA-ACEROSA (PALLAS) (GORGONACEA) [J].

BANDURRAGA, MM ;

FENICAL, W ;

DONOVAN, SF ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6463-6465

[2] ANIONIC CYCLIZATIONS OF ALPHA-ALKOXY LITHIUMS - NEW, STEREOSELECTIVE ROUTES TO SUBSTITUTED TETRAHYDROFURANS [J].

BROKA, CA ;

LEE, WJ ;

SHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1336-1338

[3] A NEW SYNTHESIS OF SUBSTITUTED FURANS [J].

DANHEISER, RL ;

STONER, EJ ;

KOYAMA, H ;

YAMASHITA, DS ;

KLADE, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4407-4413

[4] UNUSUAL NEW ALLENE CYCLIZATION REACTION - SYNTHESIS OF DIHYDROFURAN-3(2H)-ONES [J].

GANGE, D ;

MAGNUS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7746-7747

[5] A MILD METHOD FOR THE SYNTHESIS OF FURANS - APPLICATION TO 2,5-BRIDGED FURANO MACROCYCLIC-COMPOUNDS [J].

MARSHALL, JA ;

ROBINSON, ED .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3450-3451

[6] THE SYNTHESIS OF CEMBRANOLIDE PRECURSORS VIA ADDITION OF ALLYLSTANNANES TO CONJUGATED ALDEHYDES [J].

MARSHALL, JA ;

DEHOFF, BS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (06) :863-872

[7] SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .19. A VERSATILE AND SELECTIVE ROUTE TO DIFUNCTIONAL TRISUBSTITUTED (E)-ALKENE SYNTHONS VIA ZIRCONIUM-CATALYZED CARBOALUMINATION OF ALKYNES [J].

RAND, CL ;

VANHORN, DE ;

MOORE, MW ;

NEGISHI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) :4093-4096

[8]

SARGSYAN MC, 1977, ARM KHIM ZH, V30, P1000

[9] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES [J].

SONOGASHIRA, K ;

TOHDA, Y ;

HAGIHARA, N .

TETRAHEDRON LETTERS, 1975, (50) :4467-4470

[10] CYTO-TOXIC CEMBRANOIDS FROM THE GORGONIAN PSEUDOPTEROGORGIA-BIPINNATA [J].

WRIGHT, AE ;

BURRES, NS ;

SCHULTE, GK .

TETRAHEDRON LETTERS, 1989, 30 (27) :3491-3494

← 1 →