Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

Department of Chemistry of Natural Compounds University of Chemistry and Technology Prague Technická 5 160 00 Praha 6 Czech Republic

Department of Organic Chemistry Charles University Prague Hlavova 8 153 00 Praha 2 Czech Republic

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Teo Y N, Wilson J N, Kool E T. J Am Chem Soc. 2009;131:3923–3933. doi: 10.1021/ja805502k. PubMed DOI PMC

Wamhoff H, Warnecke H. ARKIVOC. 2001;9:5–100.

Novák P, Číhalová S, Otmar M, Hocek M, Kotora M. Tetrahedron. 2008;64:5200–5207. doi: 10.1016/j.tet.2008.03.046. DOI

Novák P, Pour M, Špulák M, Votruba I, Kotora M. Synthesis. 2008:3465–3472. doi: 10.1055/s-0028-1083181. DOI

Bobula T, Hocek M, Kotora M. Tetrahedron. 2010;66:530–536. doi: 10.1016/j.tet.2009.11.030. DOI

Nečas D, Hidasová D, Hocek M, Kotora M. Org Biomol Chem. 2011;9:5934–5937. doi: 10.1039/c1ob05844d. PubMed DOI

Šnajdr I, Janoušek Z, Takagaki M, Císařová I, Hosmane N S, Kotora M. Eur J Med Chem. 2014;83:389–397. doi: 10.1016/j.ejmech.2014.06.005. PubMed DOI

Hessler F, Kulhavá L, Císařová I, Otmar M, Kotora M. Synth Commun. 2014;44:1232–1239. doi: 10.1080/00397911.2013.848896. DOI

Takase M, Morikawa T, Abe H, Inouye M. Org Lett. 2003;5:625–628. doi: 10.1021/ol027210w. PubMed DOI

Adamo M F A, Pergoli R. Org Lett. 2007;9:4443–4446. doi: 10.1021/ol701794u. PubMed DOI

Heinrich D, Wagner T, Diederichsen U. Org Lett. 2007;9:5311–5314. doi: 10.1021/ol7025334. PubMed DOI

Nakahara M, Kuboyama T, Izawa A, Hari Y, Imanishi T, Obika S. Bioorg Med Chem Lett. 2009;19:3316–3319. doi: 10.1016/j.bmcl.2009.04.063. PubMed DOI

Kaliappan K P, Kalanidhi P, Mahapatra S. Synlett. 2009:2162–2166. doi: 10.1055/s-0029-1217570. DOI

Egron D, Durand T, Roland A, Vidal J-P, Rossi J-C. Synlett. 1999;4:435–437. doi: 10.1055/s-1999-3157. DOI

Jeanmart S, Taylor R J K. Tetrahedron Lett. 2005;46:9043–9048. doi: 10.1016/j.tetlet.2005.10.099. DOI

Rothman J H. J Org Chem. 2009;74:925–928. doi: 10.1021/jo801910u. PubMed DOI

Aljarilla A, López J C, Plumet J. Eur J Org Chem. 2010:6123–6143. doi: 10.1002/ejoc.201000570. DOI

Martin A R, Mohanan K, Luvino D, Floquet N, Baraguey C, Smietana M, Vasseur J-J. Org Biomol Chem. 2009;7:4369–4377. doi: 10.1039/b912616c. PubMed DOI

Tietze L F, Griesbach U, Schubert I, Bothe U, Marra A, Dondonni A. Chem – Eur J. 2003;9:1296–1302. doi: 10.1002/chem.200390148. PubMed DOI

Wei X, Carroll P J, Sneddon L G. Organometallics. 2006;25:609–621. doi: 10.1021/om050851l. DOI

Eignerová B, Janoušek Z, Dračínský M, Kotora M. Synlett. 2010:885–888. doi: 10.1055/s-0029-1219546. DOI

Sedlák D, Eignerová B, Dračínský M, Janoušek Z, Bartůněk P, Kotora M. J Organomet Chem. 2013;747:178–183. doi: 10.1016/j.jorganchem.2013.06.013. DOI

Rost D, Porta M, Gessler S, Blechert S. Tetrahedron Lett. 2008;49:5968–5971. doi: 10.1016/j.tetlet.2008.07.161. DOI

Vougioukalakis G C, Grubbs R H. Chem Rev. 2010;110:1746–1787. doi: 10.1021/cr9002424. PubMed DOI

Samojłowicz C, Bienek M, Zarecki A, Kadyrov R, Grela K. Chem Commun. 2008;47:6282–6284. doi: 10.1039/b816567j. PubMed DOI

Samojłowicz C, Borré E, Maudit M, Grela K. Adv Synth Catal. 2011;353:1993–2002. doi: 10.1002/adsc.201100053. DOI

Samojłowicz C, Bienik M, Pazio A, Makal A, Woźniak K, Poater A, Cavallo L, Wójcik J, Zdanowski K, Grela K. Chem – Eur J. 2011;17:12981–12993. doi: 10.1002/chem.201100160. PubMed DOI

Bargiggia F C, Murray W V. J Org Chem. 2005;70:9636–9639. doi: 10.1021/jo0514624. PubMed DOI

Michaut A, Boddaert T, Coquerel Y, Rodriguez J. Synthesis. 2007:2867–2871. doi: 10.1055/s-2007-983825. DOI

Prchalová E, Votruba I, Kotora M. J Fluorine Chem. 2012;141:49–57. doi: 10.1016/j.jfluchem.2012.06.005. DOI

Eignerová B, Dračínský M, Kotora M. Eur J Org Chem. 2008:4493–4499. doi: 10.1002/ejoc.200800230. DOI

Eignerová B, Slavíková B, Buděšínský M, Dračínský M, Klepetářová B, Šťastná E, Kotora M. J Med Chem. 2009;52:5753–5757. doi: 10.1021/jm900495f. PubMed DOI

Eignerova B, Sedlák D, Dračínský M, Bartůněk P, Kotora M. J Med Chem. 2010;53:6947–6953. doi: 10.1021/jm100563h. PubMed DOI

Řezanka M, Eignerová B, Jindřich J, Kotora M. Eur J Org Chem. 2010:6256–6262. doi: 10.1002/ejoc.201000807. DOI

Prchalová E, Štěpánek O, Smrček S, Kotora M. Future Med Chem. 2014;6:1201–1229. doi: 10.4155/fmc.14.53. PubMed DOI

Dondoni A, Giovannini P P, Marra A. J Chem Soc, Perkin Trans 1. 2001:2380–2388. doi: 10.1039/b106029p. DOI

Postema M H D, Piper J L. Tetrahedron Lett. 2002;43:7095–7099. doi: 10.1016/S0040-4039(02)01617-9. DOI

Dominique R, Das S K, Liu B, Nahra J, Schmor B, Gan Z, Roy R. Methods Enzymol. 2003;362:17–28. doi: 10.1016/S0076-6879(03)01002-4. PubMed DOI

Nolen N G, Kurish A J, Wong K A, Orlando M D. Tetrahedron Lett. 2003;44:2449–2453. doi: 10.1016/S0040-4039(03)00350-2. DOI

Lin Y A, Chalker J M, Davis B G. J Am Chem Soc. 2010;132:16805–16811. doi: 10.1021/ja104994d. PubMed DOI

Chen G, Schmieg J, Tsuji M, Franck R W. Org Lett. 2004;6:4077–4080. doi: 10.1021/ol0482137. PubMed DOI

Štěpánek P, Vích O, Werner L, Kniežo L, Dvořákova H, Vojtíšek P. Collect Czech Chem Commun. 2005;70:1411–1428. doi: 10.1135/cccc20051411. DOI

Liu S, Ben R N. Org Lett. 2005;7:2385–2388. doi: 10.1021/ol050677x. PubMed DOI

Voigtritter K, Ghorai S, Lipshutz B H. J Org Chem. 2011;76:4697–4702. doi: 10.1021/jo200360s. PubMed DOI PMC

Chatterjee A K, Choi T-L, Sanders D P, Grubbs R H. J Am Chem Soc. 2003;125:11360–11370. doi: 10.1021/ja0214882. PubMed DOI