Synthesis of muscothiazoles A and B: Critical role of methyl group substitution in RCM-based syntheses of macrocycles

被引：21
作者：
Commeureuc, AGJ
Murphy, JA
Dewis, ML
机构：
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[2] Int Flavors & Fragrances Inc, IFF R&D, Union Beach, NJ USA
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 16期
关键词：
D O I：
10.1021/ol034571i
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Graphics Muscothiazoles A (2b) and B (2c) have been prepared by two approaches that differ in the order of assembly of the rings. Comparative studies show that substitution of the carbon chains in substrate 5 or 12 (respective precursors to 13-membered and 14-membered rings by RCM), even by a single methyl group, can have a profound effect on increasing the efficiency of the macrocyclization.
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页码：2785 / 2788
页数：4
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共 36 条
  • [1] Enantioselective formal total synthesis of roseophilin
    Bamford, SJ
    Luker, T
    Speckamp, WN
    Hiemstra, H
    [J]. ORGANIC LETTERS, 2000, 2 (08) : 1157 - 1160
  • [2] THE STRUCTURE AND SYNTHESIS OF MUSCOPYRIDINE
    BIEMANN, K
    BUCHI, G
    WALKER, BH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (20) : 5558 - 5564
  • [3] The Cl2(PCy3)(IMes)Ru(=CHPh) catalyst:: olefin metathesis versus olefin isomerization
    Bourgeois, D
    Pancrazi, A
    Nolan, SP
    Prunet, J
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 : 247 - 252
  • [4] Bourgeois D, 2000, ANGEW CHEM INT EDIT, V39, P725, DOI 10.1002/(SICI)1521-3773(20000218)39:4<725::AID-ANIE725>3.0.CO
  • [5] 2-I
  • [6] Bourgeois D, 2000, SYNTHESIS-STUTTGART, P869
  • [7] Studies toward thiostrepton antibiotics: Assembly of the central pyridine-thiazole cluster of micrococcins
    Ciufolini, MA
    Shen, YC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) : 3804 - 3805
  • [8] Clark JS, 1997, TETRAHEDRON LETT, V38, P127
  • [9] Clark JS, 1997, TETRAHEDRON LETT, V38, P123
  • [10] Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles
    Crimmins, MT
    Choy, AL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7548 - 7549
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