3-Acyltetramic Acids: A Decades-Long Approach to a Fascinating Natural Product Family

Markus Petermichl; Rainer Schobert

doi:10.1055/s-0036-1588402

Synlett, Table of Contents

Synlett 2017; 28(06): 654-663
DOI: 10.1055/s-0036-1588402

account

3-Acyltetramic Acids: A Decades-Long Approach to a Fascinating Natural Product Family

Markus Petermichl

Organisch-chemisches Laboratorium der Universität Bayreuth, Gebäude NW I, 95440 Bayreuth, Germany Email: Rainer.Schobert@uni-bayreuth.de

,

Rainer Schobert*

Organisch-chemisches Laboratorium der Universität Bayreuth, Gebäude NW I, 95440 Bayreuth, Germany Email: Rainer.Schobert@uni-bayreuth.de

› Author Affiliations

Abstract

All articles of this category

Abstract

This account relates our quest for effective syntheses of 3-acyltetramic acids and also presents examples of our group’s increasing audacity to tackle the more intricate structural varieties of this compound class.

1 Introduction

2 A New Wittig-Based Access to Tetramic Acids

3 3-Acyltetramic Acids with Linear Side Chains

4 3-Decalinoyltetramic Acids

5 O- and N-Glycosylated 3-Acyltetramic Acids

6 Macrocyclic 3-Acyltetramic Acids

7 Miscellaneous Reactions

8 Whither to go from Here?

Key words

tetramic acids - natural products - metal chelates - bioactive compounds - Wittig reaction

Full Text

References

References
1 Royles BJ. L. Chem. Rev. 1995; 95: 1981

2a Ghisalberti EL In Studies in Natural Products Chemistry . Vol. 28/1. Atta-ur-Rahman Elsevier; Amsterdam: 2003: 109-163
2b Yoda H, Takahashi M, Sengoku T In Studies in Natural Products Chemistry . Vol. 46. Atta-ur-Rahman Elsevier; Amsterdam: 2015: 9-13 1

3 Gossauer A. Monopyrrolic Natural Compounds Including Tetramic Acid Derivatives. In Progress in the Chemistry of Organic Natural Products. Vol. 86. Herz W, Falk H, Kirby GW. Springer; Wien: 2003: 1-188
4 Schobert R, Schlenk A. Bioorg. Med. Chem. 2008; 16: 4203
5 Mo X, Li Q, Ju J. RSC Adv. 2014; 4: 50566

6a Cao S, Blodgett JA, Clardy J. Org. Lett. 2010; 12: 4652
6b Blodgett JA, Oh DC, Cao S, Currie CR, Kolter R, Clardy J. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 11692

7 Boettger D, Hertweck C. ChemBioChem 2013; 14: 28
8 Gui C, Li Q, Mo X, Qin X, Ma J, Ju J. Org. Lett. 2015; 17: 628
9 Hemmerling F, Hahn F. Beilstein J. Org. Chem. 2016; 12: 1512

10a Steyn PS, Wessels PL. Tetrahedron Lett. 1978; 47: 4707
10b Nolte MJ, Steyn PS, Wessels PL. J. Chem. Soc., Perkin Trans. 1 1980; 1057

11 Yamaguchi T, Saito K, Tsujimoto T, Yuki H. J. Heterocycl. Chem. 1976; 13: 533
12 Biersack B, Diestel R, Jagusch C, Sasse F, Schobert R. J. Inorg. Biochem. 2009; 103: 72
13 Lebrun M.-H, Duvert P, Gaudemer F, Gaudemer A, Deballon C, Boucly P. J. Inorg. Biochem. 1985; 24: 167

14a Zaghouani M, Nay B. Nat. Prod. Rep. 2016; 33: 540
14b Steyn PS, Rabie CJ. Phytochemistry 1976; 15: 1977

15 Churchill ME. A, Chen L. Chem. Rev. 2011; 111: 68
16 Murray EJ, Crowley RC, Truman A, Clarke SR, Cottam JA, Jadhav GP, Steele VR, O’Shea P, Lindholm C, Cockayne A, Chabra SR, Chan WC, Williams P. J. Med. Chem. 2014; 57: 2813
17 Jouin P, Castro B, Nisato D. J. Chem. Soc., Perkin Trans. 1 1987; 1177
18 Jones RC. F, Begley MJ, Peterson GE, Sumaria S. J. Chem. Soc., Perkin Trans. 1 1990; 1959
19 Hori K, Arai M, Nomura K, Yoshii E. Chem. Pharm. Bull. 1987; 35: 4368
20 Jeong Y.-C, Moloney MG. J. Org. Chem. 2011; 76: 1342

21a Sengoku T, Wierzejska J, Takahashi M, Yoda H. Synlett 2010; 2944
21b Sengoku T, Nagae Y, Ujihara Y, Takahashi M, Yoda H. J. Org. Chem. 2012; 77: 4391

22 Lacey RN. J. Chem. Soc. 1954; 850
23 Burke LT, Dixon DJ, Ley SV, Rodríguez F. Org. Biomol. Chem. 2005; 3: 274

24a Bestmann HJ, Sandmeier D. Angew. Chem., Int. Ed. Engl. 1975; 14: 634
24b Schobert R, Boeckman RK. Jr, Pero JE. Org. Synth. 2005; 82: 140

25 Kempf K, Raja A, Sasse F, Schobert R. J. Org. Chem. 2013; 78: 2455
26 Schobert R, Jagusch C, Melanophy C, Mullen G. Org. Biomol. Chem. 2004; 2: 3524
27 Löffler J, Schobert R. J. Chem. Soc., Perkin Trans. 1 1996; 2799

28a Bestmann HJ, Schobert R. Angew. Chem., Int. Ed. Engl. 1983; 22: 780
28b Bestmann HJ, Schobert R. Angew. Chem., Int. Ed. Engl. 1985; 24: 791
28c Ostermeier M, Schobert R. J. Org. Chem. 2014; 79: 4038

29 Schobert R, Siegfried S, Nieuwenhuyzen M, Milius W, Hampel F. J. Chem. Soc., Perkin Trans. 1 2000; 1723
30 Schlenk A, Diestel R, Sasse F, Schobert R. Chem. Eur. J. 2010; 16: 2599
31 Aoki S, Higuchi K, Ye Y, Satari R, Kobayashi M. Tetrahedron 2000; 56: 1833
32 Wang C.-Y, Wang B.-G, Wiryowidagdo S, Wray V, van Soest R, Steube KG, Guan H.-S, Proksch P, Ebel R. J. Nat. Prod. 2003; 66: 51
33 Xu J, Hasegawa M, Harada K.-I, Kobayashi H, Nagai H, Namikoshi M. Chem. Pharm. Bull. 2006; 54: 852
34 Schobert R, Jagusch C. Tetrahedron 2005; 61: 2301
35 Biersack B, Diestel R, Jagusch C, Rapp G, Sasse F, Schobert R. Chem. Biodivers. 2008; 5: 2423
36 Jagusch, C.; Bernhardt, G.; Schobert R. unpublished results.
37 Diestel R. Ph.D. Thesis 2010
38 Kempf K, Schmitt F, Bilitewski U, Schobert R. Tetrahedron 2015; 71: 5064
39 Bruckner S, Bilitewski U, Schobert R. Org. Lett. 2016; 18: 1136

40a Gänzle MG, Höltzel A, Walter J, Jung G, Hammes WP. Appl. Environ. Microbiol. 2000; 66: 4325
40b Höltzel A, Gänzle MG, Nicholson GJ, Hammes WP, Jung G. Angew. Chem. Int. Ed. 2000; 39: 2766
40c Marquardt U, Schmid D, Jung G. Synlett 2000; 1131
40d Böhme R, Jung G, Breitmaier E. Helv. Chim. Acta 2005; 88: 2837

41a Gänzle MG, Vogel RF. Appl. Environ. Microbiol. 2003; 69: 1305
41b Gänzle MG. Appl. Microbiol. Biotechnol. 2004; 64: 326

42 Schobert R, Dietrich M, Mullen G, Urbina-Gonzales J.-M. Synthesis 2006; 3902
43 Winterer M, Kempf K, Schobert R. J. Org. Chem. 2016; 81: 7336

44a Wright AD, Osterhage C, König GM. Org. Biomol. Chem. 2003; 1: 507
44b Wangun HV. K, Dahse H.-M, Hertweck C. J. Nat. Prod. 2007; 70: 1800

45a Ono M, Sakuda S, Suzuki A, Isogai A. J. Antibiot. 1997; 50: 111
45b Ono M, Sakuda S, Ikeda H, Furihata K, Nakayama J, Suzuki A, Isogai A. J. Antibiot. 1998; 51: 1019

46a Matsunaga S, Fusetani N, Kato Y. J. Am. Chem. Soc. 1991; 113: 9690
46b Schmidt EW, Harper MK, Faulkner DJ. J. Nat. Prod. 1997; 60: 779
46c Wolf D, Schmitz FJ, Qiu F, Kelly-Borges M. J. Nat. Prod. 1999; 62: 170
46d Ratnayake AS, Davis RA, Harper MK, Veltri CA, Andjelic CD, Barrows LR, Ireland CM. J. Nat. Prod. 2005; 68: 104
46e Angawi RF, Bavestrello G, Calcinai B, Dien HA, Donnarumma G, Tufano MA, Paoletti I, Grimaldi E, Chianese G, Fattorusso E, Taglialatela-Scafati O. Mar. Drugs 2011; 9: 2809
46f Sata NU, Matsunaga S, Fusetani N, van Soest RW. M. J. Nat. Prod. 1999; 62: 969
46g Kumar R, Subramani R, Feussner K.-D, Aalbersberg W. Mar. Drugs 2012; 10: 200

47 Pronin SV, Kozmin SA. J. Am. Chem. Soc. 2010; 132: 14394
48 Beiger JJ. Dissertation. Harvard University; USA: 2013. see: http://nrs.harvard.edu/urn-3:HUL.InstRepos:10974701
49 Loscher S, Schobert R. Chem. Eur. J. 2013; 19: 10619
50 Petermichl M, Loscher S, Schobert R. Angew. Chem. Int. Ed. 2016; 55: 10122 ; Angew. Chem. 2016, 128, 10276
51 Graupner PR, Carr A, Clancy E, Gilbert J, Bailey KL, Derby JA, Gerwick BC. J. Nat. Prod. 2003; 66: 1558
52 Hubbard M, Taylor WG, Bailey KL, Hynes RK. W. Environ. Exp. Bot. 2016; 132: 80
53 Schobert R, Siegfried S, Weingärtner J, Nieuwenhuyzen M. J. Chem. Soc., Perkin Trans. 1 2001; 2009
54 Haase RG, Schobert R. Org. Lett. 2016; 18: 6352
55 Yoshinari T, Ohmori K, Schrems MG, Pfaltz A, Suzuki K. Angew. Chem. Int. Ed. 2010; 49: 881
56 Barnickel B, Schobert R. J. Org. Chem. 2010; 75: 6716
57 Harras M, Bauer T, Kempe R, Schobert R. Tetrahedron 2013; 69: 3677
58 Schobert R, Siegfried S, Gordon GJ, Nieuwenhuyzen M, Allenmark S. Eur. J. Org. Chem. 2001; 1951

59a Schobert R, Gordon GJ, Bieser A, Milius W. Eur. J. Org. Chem. 2003; 3637
59b Schobert R, Siegfried S, Gordon GJ, Mulholland D, Nieuwenhuyzen M. Tetrahedron Lett. 2001; 42: 4561
59c Schobert R, Gordon GJ, Mullen G, Stehle R. Tetrahedron Lett. 2004; 45: 1121
59d Schobert R, Bieser A, Mullen G, Gordon G. Tetrahedron Lett. 2005; 46: 5459

60 Schobert R, Stehle R, Milius W. J. Org. Chem. 2003; 68: 9827
61 Breyer S. Diploma Thesis. University of Bayreuth; Germany: 2006