First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (-)-stagonolide D

被引：4
|
作者：
Kumar, A. Sravanth [1 ,2 ]
Praneeth, K. [2 ]
Srihari, P. [2 ]
Yadav, J. S. [1 ,2 ]
机构：
[1] Acad Sci & Innovat Res AcSIR, 2 Rafi Marg, New Delhi 110001, India
[2] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 06期
关键词：
Macrolides; Yamaguchi esterification; Epoxidation; Stereoselective reduction; Phytotoxic; STAGONOSPORA-CIRSII; POTENTIAL MYCOHERBICIDE; REDUCING AGENTS; STAGONOLIDE-G; ALCOHOLS; ARVENSE;
D O I：
10.1016/j.tetlet.2016.12.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first stereoselective total synthesis of nonenolide (-)-stagonolide D has been accomplished. Midland Alpine borane reduction to install hydroxyl group at C4, Henbest epoxidation to introduce epoxide stereoselectively between C7 and C8, Yamaguchi esterification and Olefin metathesis reaction are the key steps involved in the total synthesis. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：509 / 511
页数：3
相关论文
共 40 条
  • [31] Determination of absolute configuration of trimeric indole alkaloid, psychotrimine, by first asymmetric total synthesis
    Takahashi, Nobuaki
    Ito, Takeshi
    Matsuda, Yohei
    Kogure, Noriyuki
    Kitajima, Mariko
    Takayama, Hiromitsu
    CHEMICAL COMMUNICATIONS, 2010, 46 (14) : 2501 - 2503
  • [32] First total synthesis of neurotrophic diacetylene tetrol (-)-petrosiol D
    Reddy, A. Sathish
    Srihari, P.
    TETRAHEDRON LETTERS, 2013, 54 (47) : 6370 - 6372
  • [33] First total synthesis and absolute configuration of (-)-13-hydroxy-11,12-epoxy-neocembrene
    Zhang, T
    Liu, ZS
    Li, YL
    SYNTHESIS-STUTTGART, 2001, (03): : 393 - 398
  • [34] A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′-epi-Cochliomycin C
    Mahankali, Bakkolla
    Srihari, Pabbaraja
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (18) : 3983 - 3993
  • [35] First Total Synthesis of Oxirapentyn D, a Highly Oxidized Chromene Natural Product
    Sakai, Takahiro
    Suzuki, Keisuke
    Ohmori, Ken
    SYNLETT, 2018, 29 (10) : 1351 - 1357
  • [36] Stereoselective Total Synthesis of (+)-Oploxyne A, (-)-Oploxyne B, and Their C-10 Epimers and Structure Revision of Natural Oploxyne B
    Yadav, J. S.
    Boyapelly, Kumaraswamy
    Alugubelli, Sathish Reddy
    Pabbaraja, Srihari
    Vangala, Janakiram R.
    Kalivendi, Shasi V.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08): : 2568 - 2576
  • [37] Stereoselective Synthesis of 2,6-Disubstituted Piperidines Using the Iridium-Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)-241D and Related Piperidine Alkaloids
    Gnamm, Christian
    Krauter, Caroline M.
    Broedner, Kerstin
    Helmchen, Guenter
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2050 - 2054
  • [38] A General Access to Zaragozic Acids: Total Synthesis and Structure Elucidation of Zaragozic Acid D and Formal Syntheses of Zaragozic Acids A and C
    Wang, Yuzhou
    Metz, Peter
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (12) : 3335 - 3337
  • [39] Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine
    Gruner, Konstanze K.
    Hopfmann, Thomas
    Matsumoto, Kazuhiro
    Jaeger, Anne
    Katsuki, Tsutomu
    Knoelker, Hans-Joachim
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) : 2057 - 2061
  • [40] The first stereoselective total synthesis of the Z-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone
    Krishna, Palakodety Radha
    Prabhakar, Sunchu
    Krishna, Kallaganti V. S. Rama
    RSC ADVANCES, 2013, 3 (45): : 23343 - 23346
1234