Synthesis of γ-lactones and ascorbic acid analogues by diastereoselective hydrogenation of α-hydroxy-γ-alkylidenebutenolides

被引：0
|
作者：
Langer, P [1 ]
Saleh, NNR [1 ]
Köhler, V [1 ]
机构：
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 2002卷 / 09期
关键词：
butenolides; hydrogenations; lactones; silyl enol ethers; stereo selectivity;
D O I：
10.1002/1099-0690(200205)2002:9<1566::AID-EJOC1566>3.0.CO;2-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride afforded functionalized gamma-alkylidene-alpha-hydroxybutenolides, which were transformed into cis-configured gamma-lactones by diastereoselective hydrogenation. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
引用
收藏
页码：1566 / 1572
页数：7
相关论文
共 50 条
  • [1] Chelation-controlled highly diastereoselective catalytic hydrogenation of γ-hydroxy-α-methylenecarboxylic acid esters
    Nagano, H
    Yokota, M
    Iwazaki, Y
    [J]. TETRAHEDRON LETTERS, 2004, 45 (15) : 3035 - 3037
  • [2] Highly diastereoselective epimerization:: Stereodivergent synthesis of α-hydroxy-β-amino isopentanoic acid
    Seo, Woo Duck
    Curtis-Long, Marcus J.
    Ryu, Young Bae
    Lee, Jin Hwan
    Yang, Min Suk
    Lee, Woo Song
    Park, Ki Hun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13): : 5008 - 5011
  • [3] A practical diastereoselective synthesis of β-hydroxy-β-trifluoromethyl imines
    Liu, Zhen-Jiang
    Mei, Ying-Qiao
    Liu, Jin-Tao
    [J]. TETRAHEDRON, 2007, 63 (04) : 855 - 860
  • [4] Enantio- and diastereoselective hydrogenation via dynamic kinetic resolution by a cationic iridium complex in the synthesis of β-hydroxy-α-amino acid esters
    Makino, Kazuishi
    Iwasaki, Masamichi
    Hamada, Yasumasa
    [J]. ORGANIC LETTERS, 2006, 8 (20) : 4573 - 4576
  • [5] Application of silacyclic allylsilanes to the synthesis of β-hydroxy-δ-lactones: synthesis of Prelactone B
    Sellars, Jonathan D.
    Steel, Patrick G.
    [J]. TETRAHEDRON, 2009, 65 (28) : 5588 - 5595
  • [6] A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides
    Davoust, Marion
    Cantagrel, Frederic
    Metzner, Patrick
    Briere, Jean-Francois
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (11) : 1981 - 1993
  • [7] Asymmetric synthesis of β-hydroxy-α-amino acid
    Makino, K
    Hamada, Y
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (12) : 1198 - 1208
  • [8] Stereoselective synthesis of α-hydroxy-β-amino acid derivatives from β-hydroxy-γ,δ-unsaturated sulfilimine
    Raghavan, Sadagopan
    Mustafa, Shalk
    [J]. TETRAHEDRON LETTERS, 2008, 49 (20) : 3216 - 3220
  • [9] β-Aryl-δ-Hydroxy-γ-Lactones: Synthesis, Structural Analysis and Cytotoxic Activity
    Gawdzik, Barbara
    Wzorek, Alicja
    Kamizela, Angelika
    Urbaniak, Mariusz
    Gladkowski, Witold
    Lis, Magdalena
    Obminska-Mrukowicz, Bozena
    Bialonska, Agata
    [J]. CURRENT ORGANIC SYNTHESIS, 2016, 13 (06) : 901 - 906
  • [10] Synthesis of chiral β-hydroxy-δ-lactones using an epoxide-based methodology
    Vazquez-Maldonado, Luis A.
    Valentin, Elizabeth
    Torres, Gerardo
    Prieto, Jose A.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
12345