Synthesis of a vinylchlorine-containing 1,3-diol from a marine cyanophyte

Tetrahedron

Volumn 70, Issue 30, 2014, Pages 4571-4579

  Wang, Xiao Long ^a,b   Yang, Yang Yang ^b   Chen, Hui Jun ^b   Wu, Yikang ^b   Ma, Dong Sheng ^a  

^a HEILONGJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aldehydes; Diols; Epoxides; Metathesis; Natural products

Indexed keywords

ALCOHOL; ALDEHYDE; CHLORINE DERIVATIVE; EPOXIDE; HYDROXYL GROUP; IODIDE; PHENOL; VINYL CHLORIDE; VINYL DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CYANOBACTERIUM; ENVIRONMENTAL TEMPERATURE; EVAPORATION; HYDROBORATION; HYDROGENATION; HYDROLYSIS; ISOMER; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CYANOBACTERIA;

EID: 84901796762     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.04.090     Document Type: Article

References (47)

1. A.M. Burja, B. Banaigs, E. Abou-Mansour, J.G. Burgess, and P.C. Wright Tetrahedron 57 2001 9347 9377
2. J.S. Mynderse, and R.E. Moore Phytochemistry 17 1978 1325 1326 (compound 1)
3. R.T. Williamson, I.P. Singh, and W.H. Gerwick Tetrahedron 60 2004 7025 7033 (compound 3)
4. J.K. Nunnery, N. Engene, T. Byrum, Z. Cao, S.V. Jabba, A.R. Pererira, T. Matainaho, T.F. Murray, and W. Gerwick J. Org. Chem. 77 2012 4198 4208 (compound 2)
5. C. Nilewski, R.W. Geisser, and E.M. Carreira Nature 457 2009 573 576 (compound 5)
6. D.J. Edwards, B.L. Marquez, L.M. Nogle, K. McPhail, D.E. Geoger, M.A. Roberts, and W.H. Gerwick Chem. Biol. 11 2004 817 833
7. D.G. Nagle, P.U. Park, and V.J. Paul Tetrahedron Lett. 38 1997 6969 6972 (compound 4)
8. N.A. Powell, and S.D. Rychnovsky Tetrahedron Lett. 39 1998 3103 3106
9. L. He, S.-M. Zhang, Y.-K. Wu, and Y. Li Chin. J. Chem. 29 2011 2664 2668
10. S. Zhang, and Y. Wu Chin. J. Chem. 29 2011 2798 2802
11. G.-B. Ren, Y.-X. Huang, Y.-P. Sun, Z.-H. Li, and Y.-K. Wu J. Org. Chem. 75 2009 5048 5064
12. X. Yan, S.-M. Zhang, Y.-K. Wu, and P. Gao Org. Biomol. Chem. 9 2011 6797 6806
13. P. Jiang, S.-M. Zhang, L. He, Y.-K. Wu, and Y. Li Tetrahedron 67 2011 2651 2660
14. S.-M. Zhang, X.-W. Lu, and Y.-K. Wu Asian J. Org. Chem. 1 2012 245 250
15. C.-Y. Chen, W.-B. Han, H.-J. Chen, Y.-K. Wu, and P. Gao Eur. J. Org. Chem. 2013 348 355
16. Z.-L. Wan, G.-L. Zhang, H.-J. Chen, Y.-K. Wu, and Y. Li Eur. J. Org. Chem. 2014 2128 2139
17. S.D. Rychnovsky Chem. Rev. 95 1995 2021 2040
18. J. Mulzer, C. Pietschman, B. Schollhorn, J. Buschmann, and P. Luger Liebigs Ann. Chem. 1995 1433 1439 (the first report for those epoxy chiral building blocks)
19. J.-Z. Wu, J. Gao, G.-B. Ren, Z.-B. Zhen, Y.-H. Zhang, and Y.-K. Wu Tetrahedron 65 2009 289 299 (a practical route to the epoxy chiral building blocks using d-gluconolactone as the starting material)
20. J.L. Marco, and J.A. Hueso-Rodriquez Tetrahedron Lett. 29 1988 2459 2462
21. C.V. Ramana, B. Srinivas, V.G. Puranik, and M.K. Gurjar J. Org. Chem. 70 2005 8216 8219
22. R. Van Rijsbergen, M.J.O. Anteunis, and A. De Bruyn J. Carbohydr. Chem. 2 1983 395 404
23. P.J. Garegg, and B. Samuelsson Synthesis 1979 469 470
24. P.J. Garegg, and B. Samuelsson Synthesis 1979 813 814 for recent applications, cf.
25. H.B. Mereyala, P.M. Goud, R.R. Gadikota, and K.R. Reddy J. Carbohydr. Chem. 19 2000 1211 1212
26. G. Banda, and I.E. Chakravarthy Tetrahedron: Asymmetry 17 2006 1684 1687
27. J.S. Yadav, S. Das, and A.K. Mishra Tetrahedron: Asymmetry 21 2010 2443 2447
28. P.J. Garegg, and B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1980 2866 2869
29. B. Classon, P.J. Garegg, and B. Samuelsson Can. J. Chem. 59 1981 339 343
30. P.J. Garegg, R. Johansson, C. Orthega, and B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1982 681 683
31. G.S. Lemen, and J.P. Wolfe Org. Lett. 12 2010 2322 2325
32. 2O as CM reaction solvent, see: M. Abbas, A. Leitgeb, and C. Slugovc Synlett 2013 1193 1196
33. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155 4156
34. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277 7278
35. R.E. Ireland, and L.-B. Liu J. Org. Chem. 58 1993 2899-2899
36. P.J. Stevenson, A.B. Treacy, and M. Nieuwenhuyzen J. Chem. Soc., Perkin Trans. 2 1997 589 591
37. K. Takai, K. Nitta, and K. Utimoto J. Am. Chem. Soc. 108 1986 7408 7410 (the original report for the Takai reaction)
38. 3, see: N.A. Powell Studies Towards Tandem 'One-way' Bergman Radical Cyclizations of Aromatic Enediynes and Synthesis of anti-1,3-Diols by the Cationic Coupling of Nucleophiles with 4-Acetoxy-1,3-dioxanes Ph.D. Dissertation 1998 University of California Irvine, CA, USA (CAN 131:184915)
39. Z.-B. Zhen, J. Gao, and Y.-K. Wu J. Org. Chem. 73 2008 7310 7316
40. M.J. Martinelli, N.K. Nayyar, E.D. Moher, U.P. Dhokte, J.M. Pawlak, and R. Vaidyanathan Org. Lett. 1 1999 447 450
41. M.J. Martinelli, R. Vaidyanathan, J.M. Pawlak, N.K. Nayyar, U.P. Dhokte, C.W. Doecke, L.M.H. Zollars, E.D. Moher, V. Van Khau, and B. Kosmrlj J. Am. Chem. Soc. 124 2002 3578 3585
42. M.J. Martinelli, R. Vaidyanathan, and V. Van Khau Tetrahedron Lett. 41 2000 3773 3776
43. Y.-K. Wu, and P. Ahlberg J. Org. Chem. 59 1994 5076 5077
44. J.M. Behan, R.A.W. Johnstone, and M.J. Wright J. Chem. Soc., Perkin Trans. 1 1975 1216 1217
45. K. Matsuo, K. Ohtsuki, T. Yoshikawa, K. Shishido, K. Yokotani-Tomita, and M. Shindo Tetrahedron 66 2010 8407 8419
46. J. Augé, V. Boulerie, R. Gil, N. Lubin-Germain, J. Picard, and J. Uziel Synth. Commun. 33 2003 3733 3739
47. J. Mulzer, and M. Berger J. Org. Chem. 69 2004 891 898