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DOI: 10.1055/s-0037-1610287
A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D
Publication History
Received: 04 July 2018
Accepted after revision: 29 August 2018
Publication Date:
26 September 2018 (online)
Abstract
A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β-d-glucopyranosyl-(1→4)-d-galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z-alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum’s acid gave a β-keto ester that reacted with dimethyl N-methyl-d-aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N-acylation–Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.
Key words
tetramic acid - Wittig reaction - Dieckmann cyclisation - natural products - glycosylation - ancorinoside - MMP inhibitor - domino reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610287.
- Supporting Information
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References
- 1 Fujita M. Nakao Y. Matsunaga S. Seiki M. Itoh Y. van Soest RW. M. Fusetani N. Tetrahedron 2001; 57: 1229
- 2a Gialeli C. Theocharis AD. Karamanos NK. FEBS J. 2011; 278: 16
- 2b Ziyad S. Iruela-Arispe ML. Genes Cancer 2011; 2: 1085
- 2c Sounni NE. Devy L. Hajitou A. Frankenne D. Munaut C. Gilles C. Deroanne C. Thompson EW. Foidart JM. Noel A. FASEB J. 2002; 16: 555
- 3 Ohta S. Ohta E. Ikegami S. J. Org. Chem. 1997; 62: 6452
- 4 Petermichl M. Schobert R. Chem. Eur. J. 2017; 23: 14743
- 5a Ley SV. Smith SC. Woodward PR. Tetrahedron 1992; 48: 1145
- 5b Pronin SV. Kozmin SA. J. Am. Chem. Soc. 2010; 132: 14394
- 5c Loscher S. Schobert R. Chem. Eur. J. 2013; 19: 10619
- 6a Girlanda-Junges C. Keyling-Bilger F. Schmitt G. Luu B. Tetrahedron 1998; 54: 7735
- 6b Mori K. Nisho H. Liebigs Ann. Chem. 1991; 253
- 7a Adrio LA. Hii KK. Eur. J. Org. Chem. 2011; 1852
- 7b Epp JB. Widlanski TS. J. Org. Chem. 1999; 64: 293
- 8a Müller S. Schmidt RR. Helv. Chim. Acta 1993; 76: 616
- 8b Thurnhofer S. Vetter W. Tetrahedron 2007; 63: 1140
- 9 Huang Z. Zhang Y.-M. Cheng Q. Zhang J. Liu Y.-H. Wang B. Yu X.-Q. J. Mater. Chem. B 2016; 4: 5575
- 10 McDougal PG. Rico JG. Oh Y.-I. Condon BD. J. Org. Chem. 1986; 51: 3388
- 11a Mitchell AJ. Dunham NP. Martinie RJ. Berman JA. Pollock CJ. Hu K. Allen BD. Chang W.-C. Silakov A. Bollinger JM. Jr. Krebs C. Boal AK. J. Am. Chem. Soc. 2017; 139: 13830
- 11b Reid CM. Fanning KN. Fowler LS. Sutherland A. Tetrahedron 2015; 71: 245
- 12 Wunder A. Rothemund M. Schobert R. Tetrahedron 2018; 74: 5138
- 13 Frérot E. Coste J. Poncet J. Jouin P. Castro B. Tetrahedron Lett. 1992; 33: 2815
- 14a Schmidt RR. Michel J. Angew. Chem., Int. Ed. Engl. 1980; 19: 731
- 14b Schmidt RR. Angew. Chem., Int. Ed. Engl. 1986; 25: 212
- 15 Lewis AR. Reber KP. Tetrahedron Lett. 2016; 57: 1083
- 16a Ren J.-L. Zhang X.-Y. Yu B. Wang X.-X. Shao K.-P. Zhu X.-G. Liu H.-M. Eur. J. Med. Chem. 2015; 93: 321
- 16b Bruckner S. Haase R. Schobert R. Chemistry 2017; 23: 5692
- 17a Jouin P. Castro B. J. Chem. Soc., Perkin Trans. 1 1987; 1177
- 17b Xu F. Armstrong JD. III. Zhou GX. Simmons B. Hughes D. Ge Z. Grabowski EJ. J. J. Am. Chem. Soc. 2004; 126: 13002
- 19 Lovmo K. Dütz S. Harras M. Haase RG. Milius W. Schobert R. Tetrahedron Lett. 2017; 58: 4796
- 20a Hartmann O. Kalesse M. Angew. Chem. Int. Ed. 2014; 53: 7335
- 20b Corey EJ. Székely I. Shiner CS. Tetrahedron Lett. 1977; 3529
- 21a Theodorou V. Skobridis K. Tzakos GA. Ragoussis V. Tetrahedron Lett. 2007; 48: 8230
- 21b Theodorou-Kassioumis V. Biris N. Sakarellos C. Tsikaris V. Tetrahedron Lett. 2001; 42: 7703
- 22a Lovrić M. Cepanec I. Litvić M. Bartolinčić A. Vinković V. Croat. Chem. Acta 2007; 80: 109
- 22b Laganis ED. Chenard BL. Tetrahedron Lett. 1984; 25: 5831
- 22c Dean PD. G. J. Chem. Soc. 1965; 6655
- 23 Fulmer GR. Miller AJ. M. Sherden NH. Gottlieb HE. Nudelman A. Stoltz BM. Bercaw JE. Goldberg KI. Organometallics 2010; 29: 2176
- 24 Kim J. Novak BM. Macromolecules 2004; 37: 8286