Chiral 3-hydroxypyrrolidin-2-ones from a Baylis-Hillman adduct: convergent, stereoselective synthesis of a glycosidase inhibitor

被引：17
|
作者：
Galeazzi, R [1 ]
Martelli, G [1 ]
Mobbili, G [1 ]
Orena, M [1 ]
Rinaldi, S [1 ]
机构：
[1] Univ Politecn Marche, Dipartmento Sci Mat Terra, I-60131 Ancona, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 20期
关键词：
D O I：
10.1016/j.tetasy.2004.08.016
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The O-silyl derivative 4b, prepared starting from the Baylis-Hillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3249 / 3256
页数：8
相关论文
共 50 条
  • [21] Synthetic applications of Baylis-Hillman chemistry:: An efficient and solely stereoselective synthesis of (E)-α-methylcinnamic acids and potent hypolipidemic agent LK-903 from unmodified Baylis-Hillman adducts
    Das, Biswanath
    Banerjee, Joydeep
    Chowdhury, Nikhil
    Majhi, Anjoy
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) : 1725 - 1727
  • [22] The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates
    Moghaddam, Firouz Matloubi
    Foroushani, Behzad Koushki
    Sobhani, Maryam
    Masoud, Nazila
    Khodabakhshi, Mohammad Reza
    Weng, Ng Seik
    TETRAHEDRON, 2013, 69 (38) : 8169 - 8173
  • [23] Stereoselective and regioselective synthesis of N-substituted methyl 2-((azolyl)methyl)-3-arylacrylates from Baylis-Hillman acetates
    Ozenc, Aysen Koseceli
    Celik, Ilhami
    Kokten, Sule
    TURKISH JOURNAL OF CHEMISTRY, 2017, 41 (03) : 323 - 334
  • [24] New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis-Hillman Adducts
    Zhong, Ying
    Wu, Lei
    Ding, Ming-Wu
    SYNTHESIS-STUTTGART, 2012, 44 (19): : 3085 - 3089
  • [25] Synthesis of 3-benzyl-2-hydroxy-7,8-dihydro-6H-quinolin-5-ones from Baylis-Hillman adducts
    Gowrisankar, S
    Na, JE
    Lee, MJ
    Kim, JN
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (02) : 319 - 322
  • [26] Synthesis of 3,5,6-trisubstituted α-pyrones from Baylis-Hillman adducts
    Kim, Seong Jin
    Lee, Hyun Seung
    Kim, Jae Nyoung
    TETRAHEDRON LETTERS, 2007, 48 (06) : 1069 - 1072
  • [27] Facile synthesis of 1,2,3,4-tetrasubstituted pyrroles from Baylis-Hillman adducts
    Kim, Seong Jin
    Kim, Hoo Sook
    Kim, Taek Hyeon
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (09) : 1605 - 1608
  • [28] Synthesis of functionalized 3-spirocyclopropane-2-indolones from isomerised Baylis-Hillman adducts of isatin
    Shanmugam, P
    Vaithiyanathan, V
    Viswambharan, B
    TETRAHEDRON, 2006, 62 (18) : 4342 - 4348
  • [29] Synthesis of 1,3,4-trisubstituted Pyrazoles from baylis-hillman adducts
    Kim, Hoo Sook
    Kim, Sung Hwan
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (10): : 1841 - 1843
  • [30] Stereoselective 1,3-dipolar cycloadditions of nitrones derived from amino acids. Asymmetric synthesis of N-(alkoxycarbonylmethyl)-3-hydroxypyrrolidin-2-ones
    Merino, Pedro
    Greco, Graziella
    Tejero, Tomas
    Hurtado-Guerrero, Ramon
    Matute, Rosa
    Chiacchio, Ugo
    Corsaro, Antonino
    Pistara, Venerando
    Romeo, Roberto
    TETRAHEDRON, 2013, 69 (45) : 9381 - 9390
12345