Diastereoselective synthesis of 2H,5H-dihydrofurans by cobalt-mediated cycloisomerization of allyl propargyl ethers.: Application to poly-THF molecules

被引：27

作者：

Ajamian, A ^{[1
]}

Gleason, JL ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 26期

关键词：

D O I：

10.1021/ol016768l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Ally! propargyl ethers undergo cobalt-mediated cycloisomerization reactions to form dihydrofurans in good yield and with excellent diastereoselectivity. The reaction works with a range of substrates, and its utility in synthesis is exemplified by the preparation of a bistetrahydrofuran unit.

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页码：4161 / 4164

页数：4

相关论文

共 26 条

[1] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[2] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[3] THE OXIDATIVE SPIROCYCLIZATION OF 2-(OMEGA-(OH)-ALKYL)CYCLIC ENOL ETHERS BY RHENIUM(VII)-OXIDE [J].

BOYCE, RS ;

KENNEDY, RM .

TETRAHEDRON LETTERS, 1994, 35 (29) :5133-5136

[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[5] Diastereoselective formation of 5-vinylcyclopentenes from 1,6-enynes: Cobalt-mediated C-H allylic activation and formal 5-endo-dig cyclization [J].

Dolaine, R ;

Gleason, JL .

ORGANIC LETTERS, 2000, 2 (12) :1753-1756

[6] GENERAL-APPROACH TO HALOGENATED TETRAHYDROFURAN NATURAL-PRODUCTS FROM RED ALGAE OF THE GENUS LAURENCIA - TOTAL SYNTHESIS OF (+/-)-KUMAUSALLENE AND (+/-)-1-EPI-KUMAUSALLENE [J].

GRESE, TA ;

HUTCHINSON, KD ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2468-2477

[7] SYNTHESIS AND MORPHOGENETIC ACTIVITY OF DERIVATIVES AND ANALOGS OF ARYL GERANYL ETHER JUVENOIDS [J].

HAMMOCK, BD ;

GILL, SS ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1974, 22 (03) :379-385

[8] SYNTHETIC ROUTES TO 2,5-DISUBSTITUTED TETRAHYDROFURANS [J].

HARMANGE, JC ;

FIGADERE, B .

TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1711-1754

[9] EXTENSION OF SUGAR CHAINS THROUGH ACETYLENIC INTERMEDIATES .4. DERIVATIVES OF 1-PENTYNE-D-ERYTHRO(AND D-THREO)-3,4,5-TRIOL [J].

HORTON, D ;

HUGHES, JB ;

THOMSON, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) :728-&

[10]

Horton D., 1966, CARBOHYD RES, V2, P315