CC BY-NC-ND 4.0 · SynOpen 2022; 06(04): 227-237
DOI: 10.1055/a-1942-6969
paper

Total Synthesis of Marine-Derived Azole Resistant Antifungal Agent (–)-Melearoride A and Antibiotic (–)-PF1163B

Bharath Kumar Yasam
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
,
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
› Institutsangaben
Y.B. thanks the University Grants Commission, New Delhi, India for ­financial assistance in the form of a Fellowship.


IICT Communication no. IICT/Pubs./2022/207

Abstract

A flexible stereoselective and convergent cum divergent approach to the synthesis of two 13-membered macrolides through a common skeleton present in their structure is described featuring two different routes, with good overall yield. The key synthetic reactions utilized include Keck allylation, Evans asymmetric methylation, Grubbs metathesis, and Julia–Kocienski olefination.

Supporting Information



Publikationsverlauf

Eingereicht: 10. August 2022

Angenommen nach Revision: 07. September 2022

Accepted Manuscript online:
14. September 2022

Artikel online veröffentlicht:
12. Oktober 2022

© 2022. 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

  • 1 Rateb ME, Ebel R. Nat. Prod. Rep. 2011; 28: 290
  • 2 Pfaller MA, Diekema DJ. Crit. Rev. Microbiol. 2010; 36: 1
  • 3 Morgan J, Meltzer MI, Plikaytis BD, Sofair AN, Huie-White S, Wilcox S. Infect. Control Hosp. Epidemiol. 2005; 26: 540
  • 4 Okabe M, Sugita T, Kinoshita T, Koyama K. J. Nat. Prod. 2016; 79: 1208
  • 5 Nose H, Seki A, Yaguchi T, Hosoya A, Sasaki T, Hoshoko S, Shomura T. J. Antibiot. 2000; 53: 33
  • 6 Sasaki T, Nose H, Hosoya A, Yoshida S, Kawaguchi M, Watanabe T, Usui T, Ohtsuka Y, Shomura T, Takano S, Tatsuta K. J. Antibiot. 2000; 53: 38
  • 7 Nose H, Fushumi H, Seki A, Watabe H, Hoshiko S. J. Antibiot. 2002; 55: 969
  • 8 Reed CW, Fulton MG, Nance KD, Lindsley CW. Tetrahedron Lett. 2019; 60: 743
  • 9 Tatsuta K, Takano S, Ikeda Y, Nakano S, Miyazaki S. J. Antibiot. 1999; 52: 1146
  • 10 Bouazza F, Brigitte R, Bachmann C, Gesson JP. Org. Lett. 2003; 5: 4049
  • 11 Aakash S, Hosokawa S. Synlett 2019; 30: 709
    • 12a Srihari P, Harikrishna N, Sridhar Y, Kamal A. Beilstein J. Org. Chem. 2014; 10: 3122
    • 12b Srihari P, Harikrishna N, Sridhar Y, Krishnam Raju A, Kamal A. RSC Adv. 2014; 4: 37629
    • 12c Vamshikrishna K, Srinu G, Srihari P. Tetrahedron: Asymmetry 2014; 25: 203
    • 12d Sridhar Y, Srihari P. Eur. J. Org. Chem. 2013; 578
    • 12e Srihari P, Mahankali B, Rajendraprasad K. Tetrahedron Lett. 2012; 53: 56
    • 12f Srihari P, Satyanarayana K, Ganganna B, Yadav JS. J. Org. Chem. 2011; 76: 1922
    • 12g Srihari P, Sridhar Y. Eur. J. Org. Chem. 2011; 6690
    • 13a Das B, Laxminarayana K, Krishnaiah M, Nandan Kumar D. Helv. Chim. Acta 2009; 92: 1840
    • 13b Sunnam SK, Prasad KR. Tetrahedron 2014; 70: 2096
    • 13c Feng JP, Shi ZF, Zhang JT, Qi XL, Cao XP. J. Org. Chem. 2008; 73: 6873
  • 14 Harbindu A, Kumar P. Synthesis 2011; 1954
  • 15 Sabitha G, Gurumurthy CH, Yadav JS. Synthesis 2014; 46: 110
  • 16 Wei L, He GG, Liu L, Tang M, Zhang T, Bai H, Du ZT. Russ. J. Org. Chem. 2020; 56: 1089
  • 17 Chakraborty TK, Suresh VR. Tetrahedron Lett. 1998; 39: 7775
  • 18 Markku JO, Jan ET, Ari Koskinen MP. Tetrahedron 2005; 61: 10748
    • 19a Wunder A, Schobert R. Org. Biomol. Chem. 2016; 14: 9262
    • 19b Aberle NS, Lessene G, Watson KG. Org. Lett. 2006; 8: 419
    • 19c Pengbin G, Gang L, Yuxiu L, Aidang L, Ziwen W, Qingmin W. Mar. Drugs 2018; 16: 311
    • 19d Boger DL, Zhou J, Borzilleri RM, Nukui S, Castle SL. J. Org. Chem. 1997; 62: 2054
  • 20 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
  • 21 Sridhar Y, Srihari P. Org. Biomol. Chem. 2014; 12: 2950
  • 22 Erwin H, Palecek J, Jorg P, Wolfgang F. Eur. J. Org. Chem. 2009; 3765
  • 24 Kamauchi H, Kimura Y, Ushiwatari M, Suzuki M, Seki T, Takao K, Sugita Y. Bioorg. Med. Chem. 2021; 37: 127845