CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 285-290
DOI: 10.1055/a-1647-7202
paper

Stereoselective Synthesis of the C19–C39 Fragment of Bastimolide A

Nemilikonda Sravan Kumar
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
B. Janaki Ramulu
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
,
Subhash Ghosh  ∗
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
› Author AffiliationsN.S.K. thanks the University Grants Commission (UGC) New Delhi for a fellowship, and B.J.R. thanks the Science and Engineering Research Board (SERB) for a National Post Doctoral Fellowship (N-PDF).
› Further Information
   Permissions and Reprints All articles of this category


Abstract

This paper describes the synthesis of the C19–C39 fragment of the antimalarial natural product bastimolide A via addition of a functionalized C19–C26 alkyne fragment to a C27–C39 aldehyde fragment. Opening of a terminal epoxide and Noyori asymmetric reduction were used as key steps in the synthesis.

Key words

bastimolide A - antimalarial activity - stereoselective synthesis - epoxide opening - Noyori asymmetric reduction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1647-7202.
  • Supporting Information


Publication History

Received: 30 August 2021

Accepted after revision: 16 September 2021

Accepted Manuscript online:
17 September 2021

Article published online:
06 October 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Pallela R, Na-Young Y, Kim SK. Mar. Drugs 2010; 8: 1189
      CrossrefPubMed
    • 1b Kuttruff CA, Eastgate MD, Baron PS. Nat. Prod. Rep. 2014; 31: 419
      CrossrefPubMed
    • 1c Blunt JW, Copp BR, Keyzers RA, Munro MH. G, Prinsep MR. Nat. Prod. Rep. 2012; 29: 144
      CrossrefPubMed
  • 2 Shao C.-L, Linington RG, Balunas MJ, Centeno A, Boudreau P, Zhang C, Engene N, Spadafora C, Mutka TS, Kyle DE, Gerwick L, Wang C.-Y, Gerwick WH. J. Org. Chem. 2015; 80: 7849
    CrossrefPubMed
    • 3a Ghosh S, Kumar SU, Shashidhar J. J. Org. Chem. 2008; 73: 1582
      CrossrefPubMed
    • 3b Ghosh S, Pradhan TK. J. Org. Chem. 2010; 75: 2107
      CrossrefPubMed
    • 3c Athe S, Chandrasekhar B, Roy S, Pradhan TK, Ghosh S. J. Org. Chem. 2012; 77: 9840
      CrossrefPubMed
    • 3d Reddy KM, Yamini V, Singarapu KK, Ghosh S. Org. Lett. 2014; 16: 2658
      CrossrefPubMed
    • 3e Chandrasekhar B, Athe S, Reddy PP, Ghosh S. Org. Biomol. Chem. 2015; 13: 115
      CrossrefPubMed
    • 3f Rao KN, Kanakaraju M, Kunwar AC, Ghosh S. Org. Lett. 2016; 18: 4092
      CrossrefPubMed
    • 3g Athe A, Sharma A, Marumudi K, Ghosh S. Org. Biomol. Chem. 2016; 14: 6769
      CrossrefPubMed
    • 3h Sharma A, Athe S, Ghosh S. ACS Omega 2018; 3: 16563
      CrossrefPubMed
  • 4 Quintard A, Sperandio C, Rodriguez J. Org. Lett. 2018; 20: 5274
    Article in Thieme ConnectPubMed
  • 5 Schleicher DK, Jamison TF. Beilstein J. Org. Chem. 2013; 9: 1533
    CrossrefPubMed
  • 7 Sayini R, Srihari P. Synthesis 2018; 50: 663
    CrossrefPubMed
  • 8 Nicolaou KC, Daines RA, Uenishi J, Li WS, Papahatjis PD, Chakraborty TK. J. Am. Chem. Soc. 1988; 110: 4672
    CrossrefPubMed
  • 9 Bujaranipalli S, Das S. Tetrahedron: Asymmetry 2016; 27: 254
    Crossref
  • 10 Cook C, Guinchard X, Liron F, Roulland E. Org. Lett. 2010; 12: 744
    CrossrefPubMed
  • 11 Nilewski C, Deprez NR, Fessard TC, Li D, Geisser RW, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 7940
    CrossrefPubMed
  • 12 Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
    Crossref
  • 13 Matsumura K, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1997; 119: 8738
    Crossref