The furan approach to oxacycles.: Part 3:: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans

被引：33
作者：
Alonso, D
Pérez, M
Gómez, G
Covelo, B
Fall, Y [1 ]
机构：
[1] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36200, Spain
[2] Univ Vigo, Fac Quim, Dept Quim Inorgan, Vigo 36200, Spain
来源：
TETRAHEDRON | 2005年 / 61卷 / 08期
关键词：
furan; singlet oxygen; tetrahydropyran; oxacycles; marin toxins;
D O I：
10.1016/j.tet.2005.01.001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Commercially available furan 1 was converted to 2,3-trans and 2,3-cis-di substituted tetrahydropyrans 2 and 3 using a highly efficient route to oxacycles, based on the oxidation of the furan ring with singlet oxygen. Tetrahydropyrans 2 and 3 could be easily separated by column chromatography. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2021 / 2026
页数：6
相关论文
共 30 条
  • [1] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS
    ALVAREZ, E
    CANDENAS, ML
    PEREZ, R
    RAVELO, JL
    MARTIN, JD
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1953 - 1980
  • [2] Stereocontrolled synthesis of cyclic ethers by intramolecular hetero-Michael addition .5. Synthesis of all diastereoisomers of 2,3,5,6-tetrasubstituted tetrahydropyrans
    Betancort, JM
    Martin, VS
    Padron, JM
    Palazon, JM
    Ramirez, MA
    Soler, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4570 - 4583
  • [3] The cis-2-alkyl-3-oxy-tetrahydropyran unit as a building block for new ionophores with C2-symmetry
    Carrillo, R
    Martín, VS
    Martín, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (27) : 5215 - 5219
  • [4] Clark JS, 1999, TETRAHEDRON, V55, P8231
  • [5] Synthesis of seven-membered oxacycles.: Part 2:: The furan approach
    Fall, Y
    Vidal, B
    Alonso, D
    Gómez, G
    [J]. TETRAHEDRON LETTERS, 2003, 44 (24) : 4467 - 4469
  • [6] Methoxyallene, a building block for the synthesis of seven-membered oxacycles
    Fall, Y
    Gomez, G
    Fernandez, C
    [J]. TETRAHEDRON LETTERS, 1999, 40 (47) : 8307 - 8308
  • [7] Marine natural products
    Faulkner, DJ
    [J]. NATURAL PRODUCT REPORTS, 1996, 13 (02) : 75 - 125
  • [8] Total synthesis of ciguatoxin CTX3C
    Hirama, M
    Oishi, T
    Uehara, H
    Inoue, M
    Maruyama, M
    Guri, H
    Satake, M
    [J]. SCIENCE, 2001, 294 (5548) : 1904 - 1907
  • [9] Mirror image synthesis of left ends of ciguatoxin and gambiertoxin 4b
    Hosokawa, S
    Isobe, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 37 - 48
  • [10] Total synthesis of ciguatoxin CTX3C, a causative toxin of ciguatera seafood poisoning
    Inoue, M
    Hirama, M
    [J]. SYNLETT, 2004, (04) : 577 - 595
123