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Synthesis 2017; 49(02): 237-251
DOI: 10.1055/s-0035-1562540
DOI: 10.1055/s-0035-1562540
short review
Strategies for the Synthesis of Deoxypropionates
Further Information
Publication History
Received: 15 July 2016
Accepted: 22 July 2016
Publication Date:
09 September 2016 (online)
Dedicated to Professor Dieter Enders on the occasion of his 70th birthday
Abstract
Deoxypropionates constitute an important class of polyketide natural products. The biological properties of deoxypropionates are diverse and synthetic strategies toward their preparation are equally manifold. This short review presents some recent developments on the synthesis of deoxypropionate units involving, besides iterative and non-iterative routes, other methods such as stereoselective Mukaiyama reactions or lithiation–borylation–protodeboronation sequences.
1 Introduction
2 Biosynthesis of Deoxypropionates
3 Iterative Synthetic Methods
3.1 Conjugate Addition of Cuprates
3.2 Copper-Catalyzed Conjugate Additions
3.3 Copper-Mediated Allylic Substitution
3.4 Myers Alkylation
3.5 Zirconium-Catalyzed Carboalumination
3.6 Homologation of Boronates with Organolithiums
4 Non-Iterative Methods
4.1 Enzymatic Desymmetrization
4.2 Ex Chiral Pool Synthesis from Wax Esters
4.3 Ex Chiral Pool Synthesis from the Roche Ester
4.4 Sequential [3,3]-Sigmatropic Rearrangement and Catalytic Hydrogenation
5 Miscellaneous Methods
6 Conclusion
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References
- 1a O’Hagan D. The Polyketide Metabolites . Ellis Horwood; Chichester: 1991
- 1b Paterson I. Pure Appl. Chem. 1992; 64: 1821
- 1c O’Hagan D. Nat. Prod. Rep. 1995; 12: 1
- 1d Yeung K.-S, Paterson I. Chem. Rev. 2005; 105: 4237
- 1e Schetter B, Mahrwald R. Angew. Chem. Int. Ed. 2006; 45: 7506
- 1f Menche D. Nat. Prod. Rep. 2008; 25: 905
- 2 For a review on polypropionates, see: Li J, Menche D. Synthesis 2009; 2293
- 3 Norte M, Fernández JJ, Padilla A. Tetrahedron Lett. 1994; 35: 3413
- 4 Norte M, Cataldo F, González AG, Rodríguez ML, Ruiz-Perez C. Tetrahedron 1990; 46: 1669
- 5a Norte M, Cataldo F, González AG. Tetrahedron Lett. 1988; 29: 2879
- 5b Paul MC, Zubia E, Ortega MJ, Salvá J. Tetrahedron 1997; 53: 2303
- 6 Garson MJ, Small CJ, Skelton BW, Thinapong P, White AH. J. Chem. Soc., Perkin Trans 1 1990; 805
- 7 Beukes DR, Davies-Coleman MT. Tetrahedron 1999; 55: 4051
- 9 Morris BD, Smyth RR, Foster SP, Hofmann MP, Roelofs WL, Franke S, Francke W. J. Nat. Prod. 2005; 68: 26
- 10a Chow S, Fletcher MT, Lambert LK, Gallagher OP, Moore CJ, Cribb BW, Allsopp PG, Kitching W. J. Org. Chem. 2005; 70: 1808
- 10b Fletcher MT, Chow S, Lambert LK, Gallagher OP, Cribb BW, Allsopp PG, Moore CJ, Kitching W. Org. Lett. 2003; 5: 5083
- 11a Morr M, Wray V, Fortkamp J, Schmid RD. Liebigs Ann. Chem. 1992; 433
- 11b Morr M, Proppe C, Wray V. Liebigs Ann. Chem. 1995; 2001
- 12a Noll H. J. Biol. Chem. 1957; 224: 149
- 12b Ginger LG, Anderson RJ. J. Biol. Chem. 1945; 157: 203
- 12c Nakamura T, Nakogome H, Sano S, Sadayuki T, Hosokawa S. Chem. Lett. 2016; 45: 550
- 13a For a review, see: Minnikin DE, Kremer L, Dover LG, Besra GS. Chem. Biol. 2002; 9: 545
- 13b Cox JS, Chen B, McNeil M, Jacobs WR. Jr. Nature 1999; 402: 79
- 14a Goren MB, Brokl O, Das BC, Lederer E. Biochemistry 1971; 10: 72
- 14b Xu S, Oda A, Bobinski T, Li H, Matsueda Y, Negishi E.-i. Angew. Chem. Int. Ed. 2015; 54: 9319
- 15 Liu C.-M, Hermann TE. J. Biol. Chem. 1978; 253: 5892
- 16a Nara F, Tanaka M, Masuda-Inoue S, Yamasato Y, Doi-Yoshioka H, Suzuki-Konagai K, Kumakura S, Ogita T. J. Antibiot. 1999; 52: 531
- 16b Nara F, Tanaka M, Hosoya T, Suzuki-Konagai K, Ogita T. J. Antibiot. 1999; 52: 525
- 17 Wang B, You J, King JB, Cai S, Park E, Powell DR, Cichewicz RH. J. Nat. Prod. 2014; 77: 2273
- 18a Ishiwata H, Nemoto T, Ojika M, Yamada K. J. Org. Chem. 1994; 59: 4710
- 18b Bai R, Covell DG, Liu C, Ghosh AK, Hamel E. J. Biol. Chem. 2002; 277: 32165
- 19a Berger J, Jampolsky LM, Goldberg MW. Arch. Biochem. 1949; 22: 476
- 19b Trader DJ, Carlson EE. Bioorg. Med. Chem. Lett. 2015; 25: 4767
- 20a Sugawara A, Tanaka T, Hirose T, Ishiyama A, Iwatsuki M, Takahashi Y, Otoguro K, Omura S, Sunazuka T. Bioorg. Med. Chem. Lett. 2013; 23: 2302
- 20b Wilkinson B, Gregory MA, Moss SJ, Carletti I, Sheridan RM, Kaja A, Ward M, Olano C, Mendez C, Salas JA, Leadlay PF, vanGinckel R, Zhang M.-Q. Bioorg. Med. Chem. Lett. 2006; 16: 5814
- 21 Novoa EM, Camacho N, Tor A, Wilkinson B, Moss S, Marín-Garciá P, Azcárate IG, Bautista JM, Mirando AC, Francklyn CS, Varon S, Royo M, Cortés A, Ribas de Pouplana L. Proc. Natl. Acad. Sci. U.S.A. 2014; 111: E5508
- 22 Hanessian S, Giroux S, Mascitti V. Synthesis 2006; 1057
- 23 ter Horst B, Feringa BL, Minnaard AJ. Chem. Commun. 2010; 46: 2535
- 24 Laschat S, Temme O In Organic Synthesis Highlights III . Mulzer J, Waldmann H. Wiley-VCH; Weinheim: 1998: 156
- 25 Olano C, Wilkinson B, Sánchez C, Moss SJ, Sheridan R, Math V, Weston AJ, Braña AF, Martin CJ, Oliynyk M, Méndez C, Leadlay PF, Salas JA. Chem. Biol. 2004; 11: 87
- 26 Olano C, Moss SJ, Braña AF, Sheridan RM, Math V, Weston AJ, Méndez C, Leadlay PF, Wilkinson B, Salas JA. Mol. Microbiol. 2004; 52: 1745
- 27 Schulze CJ, Bray WM, Loganzo F, Lam M.-H, Szal T, Villalobos A, Koehn FE, Linington RG. J. Nat. Prod. 2014; 77: 2570
- 28 Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986; 27: 4713
- 29a Williams DR, Kissel WS, Li JJ, Mullins RJ. Tetrahedron Lett. 2002; 43: 3723
- 29b Williams DR, Nold AL, Mullins RJ. J. Org. Chem. 2004; 69: 5374
- 30 Hanessian S, Yang Y, Giroux S, Mascitti V, Ma J, Raeppel F. J. Am. Chem. Soc. 2003; 125: 13784
- 31 Hanessian S, Chahal N, Giroux S. J. Org. Chem. 2006; 71: 7403
- 32 Madduri AV. R, Minnaard AJ. Chem. Eur. J. 2010; 16: 11726
- 33 den Hartog T, van Dijken DJ, Minnaard AJ, Feringa BL. Tetrahedron: Asymmetry 2010; 21: 1574
- 34 Des Mazery R, Pullez M, López F, Harutyunyan SR, Minnaard AJ, Feringa BL. J. Am. Chem. Soc. 2005; 127: 9966
- 35 Geerdink D, Buter J, van Beek TA, Minnaard AJ. Beilstein J. Org. Chem. 2014; 10: 761
- 36 ter Horst B, Feringa BL, Minnaard AJ. Org. Lett. 2007; 9: 3013
- 37 Lum T.-K, Wang S.-Y, Loh T.-P. Org. Lett. 2008; 10: 761
- 38 Barroso S, Castelli R, Baggelaar MP, Geerdink D, ter Horst B, Casas-Arce E, Overkleeft HS, van der Marel GA, Codée JD. C, Minnaard AJ. Angew. Chem. 2012; 124: 11944
- 39 Geerdink D, Minnaard AJ. Chem. Commun. 2014; 50: 2286
- 40 Geerdink D, ter Horst B, Lepore M, Mori L, Puzo G, Hirsch AK. H, Gilleron M, de Libero G, Minnaard AJ. Chem. Sci. 2013; 4: 709
- 41 Kliman LT, Mlynarski SN, Morken JP. J. Am. Chem. Soc. 2009; 131: 13210
- 42 Breit B, Herber C. Angew. Chem. Int. Ed. 2004; 43: 3790
- 43 Herber C, Breit B. Angew. Chem. Int. Ed. 2005; 44: 5267
- 44 Herber C, Breit B. Chem. Eur. J. 2006; 12: 6684
- 45 Schmidt Y, Breit B. Org. Lett. 2009; 11: 4767
- 46 Brand GJ, Studte C, Breit B. Org. Lett. 2009; 11: 4668
- 47 Schmidt Y, Lehr K, Breuninger U, Brand G, Reiss T, Breit B. J. Org. Chem. 2010; 75: 4424
- 48a Vong BG, Abraham S, Xiang AX, Theodorakis EA. Org. Lett. 2003; 5: 1617
- 48b Vong BG, Kim SH, Abraham S, Theodorakis EA. Angew. Chem. 2004; 116: 4037
- 49 Gau B, Lemétais A, Lepore M, Garcia-Alles LF, Bourdreux Y, Mori L, Gilleron M, De Libero G, Puzo G, Beau J.-M, Prandi J. ChemBioChem 2013; 14: 2413
- 50 Novak T, Tan Z, Liang B, Negishi E. J. Am. Chem. Soc. 2005; 127: 2838
- 51 Negishi E.-i, Tan Z, Liang B, Novak T. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5782
- 52 Xu S, Oda A, Bobinski T, Li H, Matsueda Y, Negishi E.-i. Angew. Chem. 2015; 127: 9451
- 53 Balieu S, Hallett GE, Burns M, Bootwicha T, Studley J, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 4398
- 54 Nagamitsu T, Takano D, Marumoto K, Fukuda T, Furuya K, Otoguro K, Takeda K, Kuwajima I, Harigaya Y, Omura S. J. Org. Chem. 2007; 72: 2744
- 55 Yadav JS, Sengupta S, Yadav NN, Chary DN, Al Ghamdi AA. Tetrahedron Lett. 2012; 53: 5952
- 56 Yadav JS, Chary DN, Yadav NN, Sengupta S, Subba Reddy BV. Helv. Chim. Acta 2013; 96: 1968
- 57 Galeyeva Y, Morr M, Laschat S, Baro A, Nimtz M, Sasse F. Synthesis 2005; 2875
- 58 Galeyeva Y, Helbig S, Morr M, Sasse F, Nimtz M, Laschat S, Baro A. Chem. Biodivers. 2006; 3: 935
- 59 Galeyeva Y, Morr M, Sasse F, Diestel R, Laschat S, Baro A, Frey W. Z. Naturforsch. B. 2009; 64: 639
- 60 Kühnel K, Maurer SC, Galeyeva Y, Frey W, Laschat S, Urlacher VB. Adv. Synth. Catal. 2007; 349: 1451
- 61 Budde M, Morr M, Schmid RD, Urlacher VB. ChemBioChem 2006; 7: 789
- 62 Theurer M, El Baz Y, Koschorreck K, Urlacher VB, Rauhut G, Baro A, Laschat S. Eur. J. Org. Chem. 2011; 4241
- 63 Yoshimura A, Kishimoto S, Nishimura S, Otsuka S, Sakai Y, Hattori A, Kakeya H. J. Org. Chem. 2014; 79: 6858
- 64 Ghanty S, Suresh Kumar CK, Reddy BV. S. Tetrahedron: Asymmetry 2015; 26: 885
- 65 Zhou J, Burgess K. Angew. Chem. Int. Ed. 2007; 46: 1129
- 66 Duffey MO, LeTiran A, Morken J. J. Am. Chem. Soc. 2003; 125: 1458
- 67 Pischl MC, Weise CF, Haseloff S, Müller M.-A, Pfaltz A, Schneider C. Chem. Eur. J. 2014; 20: 17360
- 68 Pischl MC, Weise CF, Müller M.-A, Pfaltz A, Schneider C. Angew. Chem. Int. Ed. 2013; 52: 8968
- 69 Weise CF, Pischl MC, Pfaltz A, Schneider C. J. Org. Chem. 2012; 77: 1477
- 70 Weise CF, Pischl M, Pfaltz A, Schneider C. Chem. Commun. 2011; 47: 3248
- 71 Chen T, Altmann K.-H. Chem. Eur. J. 2015; 21: 8403
- 72 Diez PS, Micalizio GC. Angew. Chem. Int. Ed. 2012; 51: 5152
- 73 Basar N, Donnelly S, Sirat HM, Thomas EJ. Org. Biomol. Chem. 2013; 11: 8476
- 74a Kumarihamy M, Fronczek FR, Ferreira D, Jacob M, Khan SI, Nanayakkara NP. D. J. Nat. Prod. 2010; 73: 1250
- 74b Nakamura T, Harachi M, Kano T, Mukaeda Y, Hosokawa S. Org. Lett. 2013; 15: 3170
- 75 Matsui R, Seto K, Sato Y, Suzuki T, Makazaki A, Kobayashi S. Angew. Chem. Int. Ed. 2011; 50: 680
- 76 Rasappan R, Aggarwal VK. Nat. Chem. 2014; 6: 810
For reviews on polyketides, see: