Synthesis of Aculeatins A and B via Iterative Hydrolytic Kinetic Resolution

被引：12
|
作者：
Harbindu, Anand [1 ]
Kumar, Pradeep [1 ]
机构：
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
来源：
SYNTHESIS-STUTTGART | 2010年 / 09期
关键词：
hydrolytic kinetic resolution; Linchpin coupling; epoxide; spirocyclization; aculeatins; MULTICOMPONENT LINCHPIN COUPLINGS; HYPERVALENT IODINE OXIDATION; EFFICIENT TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; TERMINAL EPOXIDES; AMOMUM-ACULEATUM; CONCISE SYNTHESIS; DERIVATIVES;
D O I：
10.1055/s-0029-1218687
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and concise approach for the synthesis of aculeatins A and B starting from (+/-)-epichlorohydrin is described. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution and a Linchpin coupling as key steps.
引用
收藏
页码：1479 / 1484
页数：6
相关论文
共 50 条
  • [41] Total Synthesis of Aculeatins A and B from L-Malic Acid
    Yadav, Jhillu S.
    Rao, Yerragorla Gopala
    Chandrakanth, Dandekar
    Ravindar, Kontham
    Reddy, Basi V. Subba
    HELVETICA CHIMICA ACTA, 2010, 93 (12) : 2426 - 2432
  • [42] DNA-based hydrolytic kinetic resolution of epoxides
    Dijk, Ewold W.
    Feringa, Ben L.
    Roelfes, Gerard
    TETRAHEDRON-ASYMMETRY, 2008, 19 (20) : 2374 - 2377
  • [43] Fluorous biphasic hydrolytic kinetic resolution of terminal epoxides
    Shepperson, I
    Cavazzini, M
    Pozzi, G
    Quici, S
    JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (02) : 175 - 180
  • [44] Total Synthesis of Aculeatins A, B and D and 6-epi-Aculeatin D via an Asymmetric Aldol Approach
    Maram, Lingaiah
    Das, Biswanath
    SYNTHESIS-STUTTGART, 2014, 46 (09): : 1205 - 1210
  • [45] A New Enantioselective Synthesis of the Anticonvulsant Drug Pregabalin (Lyrica) Based on a Hydrolytic Kinetic Resolution Method
    Mujahid, Mohammad
    Muthukrishnan, Murugan
    CHIRALITY, 2013, 25 (12) : 965 - 969
  • [46] First asymmetric synthesis of the antiepileptic drug Lacosamide (Vimpat®) based on a hydrolytic kinetic resolution strategy
    Muthukrishnan, M.
    Mujahid, M.
    Sasikumar, M.
    Mujumdar, P.
    TETRAHEDRON-ASYMMETRY, 2011, 22 (12) : 1353 - 1357
  • [47] Co-catalyzed two-stereocentered hydrolytic kinetic resolution: application to the synthesis of yashabushidiols A and B and the lactone unit of compactin and mevinolin
    Gadakh, Sunita K.
    Sudalai, Arumugam
    TETRAHEDRON-ASYMMETRY, 2015, 26 (2-3) : 118 - 123
  • [48] Polyol Synthesis with β-Oxyanionic Alkyllithium Reagents: Syntheses of Aculeatins A, B, and D
    Malathong, Viengkham
    Rychnovsky, Scott D.
    ORGANIC LETTERS, 2009, 11 (18) : 4220 - 4223
  • [49] Practical access to highly enantioenriched C-3 building blocks via hydrolytic kinetic resolution
    Furrow, ME
    Schaus, SE
    Jacobsen, EN
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20): : 6776 - 6777
  • [50] An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution
    Bose, D. Sublias
    Fatima, Liyakat
    Rajender, Salla
    SYNTHESIS-STUTTGART, 2006, 11 (11): : 1863 - 1867
12345