Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2025; 57(01): 99-108
DOI: 10.1055/a-2338-4462
DOI: 10.1055/a-2338-4462
paper
Special Topic Dedicated to Prof. H. Ila
Asymmetric Total Synthesis of Lobophopyranone A and B
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.
Key words
lobophopyranone - natural products - asymmetric synthesis - Keck–Maruoka allylations - Sakurai allylation - acid-mediated cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2338-4462.
- 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
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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
- 10a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 10b Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
- 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