Synthesis 2019; 51(06): 1427-1434
DOI: 10.1055/s-0037-1611040
paper
© Georg Thieme Verlag Stuttgart · New York

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

Mopuri Sudhakar Reddy
a  Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b  Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India   Email: prkgenius@iict.res.in
,
Gembali Manikanta
a  Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
,
a  Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
› Author Affiliations
Further Information

Publication History

Received: 21 August 2018

Accepted after revision: 27 September 2018

Publication Date:
14 November 2018 (eFirst)

IICT/Pubs/2018/205

Abstract

The first asymmetric total synthesis of penicillinolide A is described. Key steps of the synthesis involve Jacobsen’s hydrolytic kinetic resolution (HKR), chelation controlled allylation, Brown’s asymmetric allylation, hydroboration, and Yamaguchi lactonization.

Supporting Information

 
  • References

    • 1a Yu X, Sun D. Molecules 2013; 18: 6230
    • 1b Fernandes P, Martens E, Pereira D. J. Antibiot. 2017; 70: 527
    • 1c Dräger G, Kirschning A, Thiericke R, Zerlin M. Nat. Prod. Rep. 1996; 13: 365
    • 1d Ferraz HM. C, Bombonato FI, Longo LS. Jr. Synthesis 2007; 3261
    • 1e Riatto VB, Pilli RA, Victor MM. Tetrahedron 2008; 64: 2279
  • 2 Lee DS, Ko W, Quang TH, Kim KS, Sohn JH, Jang JH, Ahn JS, Kim YC, Oh H. Mar. Drugs 2013; 11: 4510
    • 3a Radha Krishna P, Narasimha Reddy PV. Tetrahedron Lett. 2006; 47: 7473
    • 3b Radha Krishna P, Narsingam M. Synthesis 2007; 3627
    • 3c Radha Krishna P, Sreeshailam A. Synlett 2008; 2795
    • 3d Radha Krishna P, Jagannadha Rao T. Tetrahedron Lett. 2010; 51: 4017
    • 3e Radha Krishna P, Jagannadha Rao T. Org. Biomol. Chem. 2010; 8: 3130
    • 3f Radha Krishna P, Ramana DV. J. Org. Chem. 2012; 77: 674
    • 3g Radha Krishna P, Prabhakara S, Rama Krishna KV. S. RSC Adv. 2013; 3: 23343
    • 3h Manikanta G, Raju G, Radha Krishna P. RSC Adv. 2015; 5: 7964
    • 3i Manikanta G, Nagaraju T. Synthesis 2016; 48: 4213
    • 3j Manikanta G, Radha Krishna P. Tetrahedron Lett. 2018; 59: 2893
  • 4 Inanaga J, Hirata K, Sacki H, Hatsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
    • 5a Das B, Laxminarayana K, Krishnaiah M, Nandan Kumar D. Helv. Chim. Acta 2009; 92: 1840
    • 5b Sunnam SK, Prasad KR. Tetrahedron 2014; 70: 2096
  • 6 Harbindu A, Kumar P. Synthesis 2011; 1954
    • 7a Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN. Science 1997; 277: 936
    • 7b Ready JM, Jacobsen EN. J. Am. Chem Soc. 2001; 123: 2687
    • 8a Hosomi A, Sakurai H. Tetrahedron Lett. 1976; 1295
    • 8b Hama N, Aoki T, Miwa S, Yamazaki M, Sato T, Chida N. Org. Lett. 2011; 13: 616
  • 9 Yu W, Mei Y, Kang Y, Hua Z, Jin Z. Org. Lett. 2004; 6: 3217
    • 10a Ramachandran PV, Chen G.-M, Brown HC. Tetrahedron Lett. 1997; 38: 2417
    • 10b Ramachandran PV. Aldrichimica Acta 2002; 35: 23