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
Download PDF
Synthesis 2016; 48(14): 2263-2270
DOI: 10.1055/s-0035-1560434
DOI: 10.1055/s-0035-1560434
paper
A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
Authors
Further Information
Publication History
Received: 02 December 2015
Accepted after revision: 29 February 2016
Publication Date:
11 April 2016 (online)
Abstract
A strategy toward the biomimetic synthesis of morusalbanol A pentamethyl ether is described. The synthesis is based on a hydrogen-bond-assisted Diels–Alder cycloaddition between a dehydroprenyl diene and a chalcone dienophile. Selective cleavage of the ortho-methyl ether of the resulting cycloadduct allows rotation of the C3–C21 bond and subsequent intramolecular cyclization affords the pentamethyl ether of (±)-morusalbanol A. As with the natural product, morusalbanol A, a number of key proton and carbon signals are absent in the NMR spectra of the title product.
Key words
morusalbanol A - Diels–Alder reaction - mulberry - Morus alba - biomimetic synthesis - natural productsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560434.
- Supporting Information (PDF)
-
References
- 1 Chen H.-D, Ding Y.-Q, Yang S.-P, Li X.-C, Wang X.-J, Zhang H.-Y, Ferreira D, Yue J.-M. Tetrahedron 2012; 68: 6054
- 2 Tan Y.-X, Yan R.-Y, Wang H.-Q, Chen R.-Y, Yu D.-Q. Planta Med. 2009; 75: 249
- 3 Abegaz BM, Ngadjui BT, Dongo E, Ngameni B, Nindi MN, Bezabih M. Phytochemistry 2002; 59: 877
- 4a Fukai T, Hano Y, Hirakura K, Nomura T, Uzawa J, Fukushima K. Chem. Pharm. Bull. 1985; 33: 3195
- 4b Nomura T In Progress in the Chemistry of Organic Natural Products . Vol. 53. Herz W, Grisebach H, Kirby GW, Tamm Ch. Springer-Verlag; New York: 1988: 87-201
- 5a Hano Y, Nomura T, Ueda S. Chem. Pharm. Bull. 1989; 37: 554
- 5b Hano Y, Nomura T, Ueda S. Can. J. Chem. 1994; 2: 12
- 5c Hano Y, Nomura T, Ueda S. J. Chem. Soc., Chem. Commun. 1990; 611
- 5d Nomura T, Fukai T, Narita T, Terada S, Uzawa J, Iitaka Y, Takasugi M, Ishikawa SI, Nagao S, Masamune T. Tetrahedron Lett. 1981; 22: 2195
- 5e Chee CF, Lee YK, Buckle MJ. C, Rahman NA. Tetrahedron Lett. 2011; 52: 1797
- 5f Cong H, Porco JA. Jr. Org. Lett. 2012; 14: 2516
- 5g Qi C, Cong H, Cahill KJ, Müller P, Johnson RP, Porco JA. Jr. Angew. Chem. Int. Ed. 2013; 52: 8345
- 5h Gunawan C, Rizzacasa MA. Org. Lett. 2010; 12: 1388
- 5i Boonsri S, Gunawan C, Krenske EH, Rizzacasa MA. Org. Biomol. Chem. 2012; 10: 6010
- 5j Han J, Li X, Guan Y, Zhao W, Wulff WD, Lei X. Angew. Chem. Int. Ed. 2014; 53: 9257
- 5k For a recent review, see: Han J, Jones AX, Lei X. Synthesis 2015; 47: 1519
- 5l Gao L, Han J, Lei X. Org. Lett. 2016; 18: 360
- 6 Tee JT, Chee CF, Buckle MJ. C, Lee VS, Chong WL, Khaledi H, Rahman NA. Tetrahedron Lett. 2015; 56: 5082
- 7 See the Supporting Information for details of the DFT calculations
- 8 Wang H, Yan Z, Lei Y, Sheng K, Yao Q, Lu K, Yu P. Tetrahedron Lett. 2014; 55: 897
- 9 Arkoudis E, Lykakis IN, Gryparis C, Stratakis M. Org. Lett. 2009; 11: 2988
- 10 Compound 23 was prepared according to our previous report, see ref. 5e.
- 11 CCDC 1402220 (21) and 1402153 (22) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 12 Napolitano CJ, McArdle P, Murphy PV. J. Org. Chem. 2010; 75: 7404
- 13 Gerecke M, Kyburz E, Planta CV, Brossi A. Helv. Chim. Acta 1962; 45: 2241
- 14 Devakaram R, Black DStC, Andrews KT, Fisher GM, Davis RA, Kumar N. Bioorg. Med. Chem. 2011; 19: 5199