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.

引用

页码：4161 / 4164

页数：4

共 26 条

[1] Annonaceous acetogenins: Recent progress
Alali, FQ
Liu, XX
McLaughlin, JL
[J]. 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
BOIVIN, TLB
[J]. TETRAHEDRON, 1987, 43 (15) : 3309 - 3362
[3] THE OXIDATIVE SPIROCYCLIZATION OF 2-(OMEGA-(OH)-ALKYL)CYCLIC ENOL ETHERS BY RHENIUM(VII)-OXIDE
BOYCE, RS
KENNEDY, RM
[J]. TETRAHEDRON LETTERS, 1994, 35 (29) : 5133 - 5136
[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
KATSUKI, T
MARTIN, VS
SHARPLESS, KB
[J]. 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
Dolaine, R
Gleason, JL
[J]. 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
GRESE, TA
HUTCHINSON, KD
OVERMAN, LE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) : 2468 - 2477
[7] SYNTHESIS AND MORPHOGENETIC ACTIVITY OF DERIVATIVES AND ANALOGS OF ARYL GERANYL ETHER JUVENOIDS
HAMMOCK, BD
GILL, SS
CASIDA, JE
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1974, 22 (03) : 379 - 385
[8] SYNTHETIC ROUTES TO 2,5-DISUBSTITUTED TETRAHYDROFURANS
HARMANGE, JC
FIGADERE, B
[J]. 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
HORTON, D
HUGHES, JB
THOMSON, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) : 728 - &
[10] Horton D., 1966, CARBOHYD RES, V2, P315

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