Synthesis 2022; 54(12): 2778-2786
DOI: 10.1055/a-1771-3564
short review

Synthetic Studies on Chromone Natural Products: The Preusso­chromones

Marc Paul Beller
,
Ulrich Koert
Financial support by the Deutsche Forschungsgemeinschaft (Ko 1349/20-1) is gratefully acknowledged.


Abstract

Total syntheses of preussochromones A, D, E, and F and structural revisions of preussochromones E and F are reviewed, demonstrating the use of α-keto esters and α,β-diketo esters as valuable reactants in stereoselective cyclization reactions in total synthesis.

1 Introduction

2 The Route to Preussochromone D

3 Synthesis and Structural Revision of Preussochromones E and F

4 Total Synthesis of Preussochromone A

5 Conclusion



Publication History

Received: 20 January 2022

Accepted after revision: 14 February 2022

Accepted Manuscript online:
14 February 2022

Article published online:
29 March 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
    • 1b Masters K.-S, Bräse S. Chem. Rev. 2012; 112: 3717
    • 2a Zhang M, Gong Y, Zhou W, Zhou Y, Liu X.-L. Org. Chem. Front. 2021; 8: 3968
    • 2b Keri RS, Budagumpi S, Pai RK, Balakrishna RG. Eur. J. Med. Chem. 2014; 78: 340
    • 3a Turner WB. J. Chem. Soc., Perkin Trans. 1 1978; 1621
    • 3b Siddiqui IN, Zahoor A, Hussain H, Ahmed I, Ahmad VU, Padula D, Draeger S, Schulz B, Meier K, Steinert M, Kurtán T, Flörke U, Pescitelli G, Krohn K. J. Nat. Prod. 2011; 74: 365
    • 3c Nising CF, Ohnemüller UK, Bräse S. Angew. Chem. Int. Ed. 2005; 45: 307 ; Angew. Chem. 2005, 118, 313
    • 3d Nicolaou KC, Li A. Angew. Chem. Int. Ed. 2008; 47: 6579 ; Angew. Chem. 2008, 120, 6681
    • 3e Tietze LF, Jackenkroll S, Raith C, Spiegl DA, Reiner JR, Ochoa Campos MC. Chemistry 2013; 19: 4876
  • 4 Wang Y, Zheng Z, Liu S, Zhang H, Li E, Guo L, Che Y. J. Nat. Prod. 2010; 73: 920
  • 5 Römpp Encyclopedia Natural Products, 1st ed. Lang Fugmann S, Fugmann B, Steglich W. Georg Thieme Verlag; Stuttgart: 2000
    • 6a Cai S, King JB, Du L, Powell DR, Cichewicz RH. J. Nat. Prod. 2014; 77: 2280
    • 6b Zhang W, Krohn K, Flörke U, Pescitelli G, Di Bari L, Antus S, Kurtán T, Rheinheimer J, Draeger S, Schulz B. Chemistry 2008; 14: 4913
  • 7 Horan RF, Sheffer AL, Austen K. J. Allergy Clin. Immunol. 1990; 85: 852
  • 8 Keam SJ, Lyseng-Williamson KA, Goa KL. Drugs 2003; 63: 991
    • 9a Wu X, Iwata T, Scharf A, Qin T, Reichl KD, Porco JA. Jr. J. Am. Chem. Soc. 2018; 140: 5969
    • 9b Qi C, Xiong Y, Eschenbrenner-Lux V, Cong H, Porco JA. Jr. J. Am. Chem. Soc. 2016; 138: 798
    • 9c Qi C, Qin T, Suzuki D, Porco JA. Jr. J. Am. Chem. Soc. 2014; 136: 3374
    • 9d Qin T, Porco JA. Jr. Angew. Chem. Int. Ed. 2014; 53: 3107
    • 9e Bröhmer MC, Boourcet E, Nieger M, Bräse S. Chem. Eur. J. 2011; 17: 13706
    • 9f Malefo MS, Ramadwa TE, Famuyide IM, McGaw LJ, Eloff JN, Sonopo S, Selepe MA. J. Nat. Prod. 2020; 83: 2508
    • 9g Liu J, Li Z, Tong P, Xie Z, Zhang Y, Li Y. J. Org. Chem. 2015; 80: 1632
    • 9h Tietze LF, Gericke KM, Singidi RR. Angew. Chem. Int. Ed. 2006; 45: 6990 ; Angew. Chem. 2006, 118, 7146
  • 10 Zhang F, Li L, Niu S, Si Y, Guo L, Jiang X, Che Y. J. Nat. Prod. 2012; 75: 230
  • 11 Ferreira AJ, Beaudry CM. Tetrahedron 2017; 73: 965
    • 12a Chen H, Jiang W, Zeng Q. Chem. Rec. 2020; 20: 1269
    • 12b Wang N, Saidhareddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246
    • 13a Kerste E, Harms K, Koert U. Org. Lett. 2019; 21: 4374
    • 13b Kerste E, Beller MP, Koert U. Eur. J. Org. Chem. 2020; 3699
  • 14 Beller MP, Ivlev S, Koert U. Org. Lett. 2022; 24: 912
  • 15 Beller MP, Harms K, Koert U. Org. Lett. 2020; 22: 6127
    • 16a Schütte J, Kilgenstein F, Fischer M, Koert U. Eur. J. Org. Chem. 2014; 5302
    • 16b Seitz T, Harms K, Koert U. Synthesis 2014; 46: 381
    • 16c Selter L, Zygalski L, Kerste E, Koert U. Synthesis 2016; 49: 17
    • 16d Smith AB, Liu Z. Org. Lett. 2008; 10: 4363
    • 16e Wohlfahrt M, Harms K, Koert U. Angew. Chem. Int. Ed. 2011; 50: 8404 ; Angew. Chem. 2011, 123, 8554
    • 16f Wohlfahrt M, Harms K, Koert U. Eur. J. Org. Chem. 2012; 2260
    • 16g Wasserman HH, Parr J. Acc. Chem. Res. 2004; 37: 687
    • 16h Wasserman HH. Aldrichimica Acta 1987; 20: 63
    • 17a Korenaga T, Hayashi K, Akaki Y, Maenishi R, Sakai T. Org. Lett. 2011; 13: 2022
    • 17b Meng L, Jin MY, Wang J. Org. Lett. 2016; 18: 4986
    • 17c Vila C, Hornillos V, Fañanás-Mastral M, Feringa BL. Chem. Commun. 2013; 49: 5933
  • 18 Kiyooka S, Kaneko Y, Komura M, Matsuo H, Nakano M. J. Org. Chem. 1991; 56: 2276
  • 19 Truong P, Shanahan CS, Doyle MP. Org. Lett. 2012; 14: 3608
  • 20 Iguchi S, Nakai H, Hayashi M, Yamamoto H. J. Org. Chem. 1979; 44: 1363
  • 21 Langer P, Saleh NN. R, Freifeld I. Chem. Commun. 2002; 168
  • 22 Matsubara S, Sugihara M, Utimoto K. Synlett 1998; 313
  • 23 Fleming I, Iqbal J. Tetrahedron Lett. 1983; 24: 327
    • 25a Lee GH, Ha SJ, Pak CS. Synth. Commun. 1999; 29: 3155
    • 25b Lee GH, Ha SJ, Pak CS. Synth. Commun. 1999; 29: 2677
    • 25c Lee GH, Pak CS. Synth. Commun. 1999; 29: 2539
    • 26a Ramulu U, Ramesh D, Rajaram S, Reddy SP, Venkatesham K, Venkateswarlu Y. Tetrahedron: Asymmetry 2012; 23: 117
    • 26b Pavan Kumar C, Ravinder M, Kumar S, Rao V. Synthesis 2011; 1320
    • 26c Babine RE. Tetrahedron Lett. 1986; 27: 5791