Synthesis
DOI: 10.1055/a-2338-4462
paper
Special Topic Dedicated to Prof. H. Ila

Asymmetric Total Synthesis of Lobophopyranone A and B

G. Sudhakar Reddy
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Utkal Mani Choudhury
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
H. Sai Keerthana
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
,
K. Charan Naik
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Debendra K. Mohapatra
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
› Author Affiliations
The authors gratefully acknowledge the financial support received from the Department of Science and Technology-Science and Engineering Research Board (DST-SERB), New Delhi, India, through Grant No. EMR/2017/002298.


Dedicated to Prof. H. Ila on her 80th Birthday celebrations, JNCASR, Bangalore, India

Abstract

The first asymmetric total synthesis and structural confirmation of lobophopyranone A and B have been accomplished from commercially available starting materials. Reagent-controlled Keck–Maruoka allylation, Grignard reaction, chelation-controlled Sakurai allylation, and acid-mediated one-step TBS ether deprotection followed by cyclization are the crucial stages in this synthesis that create the 2,6-disubstituted dihydropyranone component.

Supporting Information



Publication History

Received: 06 May 2024

Accepted after revision: 04 June 2024

Accepted Manuscript online:
04 June 2024

Article published online:
08 July 2024

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  • References

  • 1 Gradillas A, Castells JP. Angew. Chem. Int. Ed. 2006; 45: 6086
    • 2a Faul MM, Huff BE. Chem. Rev. 2000; 100: 2407
    • 2b Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063
    • 2c Danishefsky SJ, Biolodeau MT. Angew. Chem., Int. Ed. Engl. 1996; 35: 1380
    • 3a Hosoya T, Takagi M, Shinya K. J. Antibiot. 2013; 66: 235
    • 3b Asai T, Chung YM, Sakurai H, Ozeki T, Chang FR, Yamashita K, Oshima Y. Org. Lett. 2012; 14: 513
    • 3c Batista JM. Jr, Batista AN. L, Mota JS, Cass QB, Kato MJ, Bolzani VS, Freedman TB, López SN, Furlan M, Nafie LA. J. Org. Chem. 2011; 76: 2603
    • 3d Mota JS, Leite AC, Batista JM. Jr, López SN, Ambrósio DL, Passerini GD, Kato MJ, Bolzani VS, Cicarelli RM. B, Furlan M. Planta Med. 2009; 75: 620
    • 3e Tanaka T, Asai F, Iinuma M. Phytochemistry 1998; 49: 229
    • 3f Fujita T, Inoue K, Yamamoto S, Ikumoto T, Sasaki S, Toyama R, Chiba K, Hoshino Y, Okumoto T. J. Antibiot. 1994; 47: 208
    • 4a Gutiérrez-Cepeda A, Fernández JJ, Norte M, Montalvao S, Tammela P, Souto ML. J. Nat. Prod. 2015; 78: 1716
    • 4b Morais-Urano RP, Chagas AC. S, Berlinck RG. S. Exp. Parasitol. 2012; 132: 362
    • 4c Cantillo-Ciau Z, Moo-Puc R, Quijano L, Freile-Pelegrin Y. Mar. Drugs 2010; 8: 1292
    • 4d Blain JC, Mok Y.-F, Kubanek J, Allingham JS. Chem. Biol. 2010; 17: 802
    • 4e Medeiros VP, Queiroz KS. C, Cardoso ML, Monteiro GR. G, Oliveira FW, Chavante SF, Guimaraes LA, Rocha HA. O, Leite EL. Biochemistry 2008; 73: 1018
    • 4f Queiroz KS. C, Medeiros VP, Queiroz LS, Abreu LR. D, Rocha HA. O, Ferreira CV, Jucá MB, Aoyama H, Leite EL. Biomed. Pharmacother. 2008; 62: 303
    • 4g Kubanek J, Jensen PR, Keifer PA, Sullards MC, Collins DO, Fenical W. Proc. Natl. Acad. Sci. U.S.A. 2003; 100: 6916
    • 4h Compagnone RC, Pina IC, Rangel HR, Dagger F, Suárez AI, Reddy MV. R, Faulkner DJ. Tetrahedron 1998; 54: 3057
    • 4i Fontana A, Ishibashi M, Kobayashi J. Tetrahedron 1998; 54: 2041
    • 4j Rudi A, Kashman Y. J. Nat. Prod. 1993; 56: 1827
    • 4k Gunasekera SP, Gunasekera M, Gunawardana G, McCarthy P, Burres N. J. Nat. Prod. 1990; 53: 669
    • 5a Padhi B, Reddy GS, Mallampudi NA, Choudhury UM, Mohapatra DK. Org. Biomol. Chem. 2020; 18: 2685
    • 5b Srinivas B, Reddy DS, Mallampudi NA, Mohapatra DK. Org. Lett. 2018; 20: 6910
    • 5c Reddy GS, Padhi B, Bharath Y, Mohapatra DK. Org. Lett. 2017; 19: 6506
    • 5d Reddy DS, Mohapatra DK. Eur. J. Org. Chem. 2013; 1051
    • 5e Mohapatra DK, Bhimireddy E, Krishnarao PS, Das PP, Yadav JS. Org. Lett. 2011; 13: 744
    • 5f Yadav JS, Pattanayak MR, Das PP, Mohapatra DK. Org. Lett. 2011; 13: 1710
    • 5g Mohapatra DK, Das PP, Sai Reddy D, Yadav JS. Tetrahedron Lett. 2009; 50: 5941
    • 6a Frigerio M, Santagostino M, Sputore S, Palmisano G. J. Org. Chem. 1995; 60: 7272
    • 6b Frigerio M, Santagostino M. Tetrahedron Lett. 1994; 35: 8019
    • 7a Hanawa H, Hashimoto T, Maruoka K. J. Am. Chem. Soc. 2003; 125: 1708
    • 7b Hanawa H, Uraguchi D, Konishi S, Hashimoto T, Maruoka K. Chem. Eur. J. 2003; 9: 4405
    • 7c Keck GE, Tarbet KH, Geraci LS. J. Am. Chem. Soc. 1993; 115: 8467
    • 7d Keck GE, Geraci LS. Tetrahedron Lett. 1993; 34: 7827
    • 7e Wang Y, O’Doherty GA. J. Org. Chem. 2022; 87: 6006
    • 7f Yang P.-Y, Liu K, Ngai MH, Lear MJ, Wenk MR, Yao SQ. J. Am. Chem. Soc. 2010; 132: 656
  • 8 Corey EJ, Venkateswarlu A. J. Am. Chem. Soc. 1972; 94: 6190
  • 9 Yu W, Mei Y, Hua Z, Jin Z.. Org. Lett. 2004; 6: 3217
  • 11 VanRheenen V, Kelly RC, Cha DY. Tetrahedron Lett. 1976; 1973
  • 12 Zhong Y.-L, Shing TK. M. J. Org. Chem. 1997; 62: 2622
  • 13 Wang H, Shuhler BJ, Xian M. J. Org. Chem. 2007; 72: 4280
  • 14 Dirat O, Kouklovsky C, Langlois Y. Org. Lett. 1999; 1: 753
  • 15 Keck GE, Boden EP. Tetrahedron Lett. 1984; 25: 265
  • 16 Mitsunobu O, Yamada M. Bull. Chem. Soc. Jpn. 1967; 40: 2380
  • 17 Liu H.-J, Yip J, Shia K.-S. Tetrahedron Lett. 1997; 38: 2253