SYNTHESIS OF PRINCIPAL BUILDING BLOCKS OF AMPHIDINOLIDES OF THE G AND H FAMILIES

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Abstract

Based on the reactions of diastereoselective allylation of (R)-2,3-O-cyclohexylideneelyceraldehyde with methyl 3-(bromomethyl)but-3-enoate and its allylstannyl derivative, unsaturated lactones (6R)- and (6S)-6-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2H-pyran-2-ones were synthesized. After highly diastereoselective reduction, these lactones found application in the implementation of a new retrosynthetic scheme for the preparation of C5–C14, C15–C19 and C20–C26 building blocks of amphidinolides of the G and H families.

About the authors

I. V. Mineyeva

Belarusian State University; Institute for Physical Chemical Problems of the Belarusian State University

Email: i.mineyeva@yandex.ru
Minsk, Belarus

References

  1. Kobayashi J. J. Nat. Prod. 1989, 52 (2), 225–238. doi: 10.1021/np50062a001
  2. Kobayashi J., Ishibashi M., Nakamura H., Ohizumi Y., Yamasu T., Hirata Y., Sasaki T., Ohta T., Nozoe S. J. Nat. Prod. 1989, 52 (5), 1036–1041. doi: 10.1021/np50065a021
  3. Kobayashi J., Tsuda M. Nat. Prod. Rep. 2004, 21 (1), 77–93. doi 10.1039/ b310427n
  4. Fürstner A. Israel J. Chem. 2011, 51 (3–4), 329–345. doi: 10.1002/ijch.201100006C
  5. Chakraborty T.K., Suresh V.R. Tetrahedron Lett. 1998, 39 (42), 7775–7778. doi: 10.1016/S0040-4039(98)01699-2
  6. Matsunaga K., Nakatani K., Ishibashi M., Kobayashi J., Ohizumi Y. Biochem. Biophys. Acta. 1999, 1427 (1), 24–32. doi: 10.1016/S0304-4165(98)00175-5
  7. Kobayashi J., Tsuda M., Ishibashi M. Pure Appl. Chem. 1999, 71 (6), 1123–1126. doi: 10.1351/pac199971061123
  8. Chakraborty T., Das S. Curr. Med. Chem. Anti-Cancer Agents. 2001, 1 (2), 131–149. doi: 10.2174/1568011013354660
  9. Nicholas G.M., Phillips A.J. Nat. Prod. Rep. 2006, 23 (1), 79–99. doi: 10.1039/B501014B
  10. Trigili C., Pera B., Barbazanges M., Cossy J., Meyer C., Pineda O., Rodríguez-Escrich C., Urpí F., Vilarrasa J., Díaz J. F., Barasoain I. ChemBioChem. 2011, 12 (7), 1027–1030. doi: 10.1002/cbic.201100042
  11. Hara A., Morimoto R., Iwasaki Y., Saitoh T., Ishikawa Y., Nishiyama S. Angew. Chem. Int. Ed. 2012, 51 (39), 9877–9880. doi: 10.1002/anie.201204992
  12. Chakraborty T.K., Suresh V.R. Tetrahedron Lett. 1998, 39 (49), 9109–9112. doi: 10.1016/S0040-4039(98)02009-7
  13. Kobayashi J., Shimbo K., Sato M., Shiro M., Tsuda M. Org. Lett. 2000, 2 (18), 2805–2807. doi: 10.1021/ol006223b
  14. Kobayashi J., Shimbo K., Sato M., Tsuda M. J. Org. Chem. 2002, 67 (19), 6585–6592. doi org/10.1021/jo016222c
  15. Formentín P., Murga J., Carda M., Alberto Marco J. Tetrahedron: Asymmetry. 2006, 17 (20), 2938–2942. doi: 10.1016/j.tetasy.2006.10.024
  16. Petri A.F., Schneekloth J.S., Mandal A.K., Crews C.M. Org. Lett. 2007, 9 (16), 3001–3004. doi: 10.1021/ol071024e
  17. Fürstner A., Bouchez L.C., Funel J.-A., Liepins V., Porée F.-H., Gilmour R., Beaufils F., Laurich D., Tamiya M. Angew. Chem. Int. Ed. 2007, 46 (48), 9265–9270. doi: 10.1002/anie.200704024
  18. Fürstner A., Bouchez L.C., Morency L., Funel J.-A., Liepins V., Porée F.-H., Gilmour R., Laurich D., Beaufils F., Tamiya M. Chem. Eur. J. 2009, 15 (16), 3983–4010. doi: 10.1002/chem.200802067
  19. Hara A., Morimoto R., Ishikawa Y., Nishiyama S. Org. Lett. 2011, 13 (15), 4036–4039. doi: 10.1021/ol201547q
  20. García-Fortanet J., Formentín P., Díaz-Oltra S., Murga J., Carda M., Alberto Marco J. Tetrahedron. 2013, 69 (15), 3192–3196. doi: 10.1016/j.tet.2013.02.062
  21. Liesener F.P., Kalesse M. Synlett. 2005, 2005, 14, 2236–2238. doi: 10.1055/s-2005-872236
  22. Shimbo K., Nozawa K., Tsuda M., Kobayashi J. Bioorg. Med. Chem. 2005, 13 (17), 5066–5071. doi: 10.1016/j.bmc.2005.04.021
  23. Liesener F.P., Jannsen U., Kalesse M. Synthesis. 2006, 2006 (15), 2590–2602. doi: 10.1055/s-2006-942459
  24. Deng L., Ma Z., Zhang Y., Zhao G. Synlett. 2007, 2007 (1), 87–90. doi: 10.1055/s-2006-956498
  25. Deng L., Ma Z., Zhao G. Synlett. 2008, 2008 (5), 728–734. doi: 10.1055/s-2008-1032101
  26. Mineeva I.V., Kulinkovich O.G. Russ. J. Org. Chem. 2008, 44 (9), 1261–1266. doi: 10.1134/S1070428008090029
  27. Mineyeva I.V., Kulinkovich O.G. Tetrahedron Letters. 2010, 51 (14), 1836–1839. doi: 10.1016/j.tetlet.2010.01.120
  28. Mineeva I.V. Russ. J. Org. Chem. 2019, 55 (8), 1112–1123. doi: 10.1134/S1070428019080098
  29. Mineeva I.V. Russ. J. Org. Chem. 2020, 56 (6), 994–1000. doi: 10.1134/S1070428020060056
  30. Варанчук В.В., Минеева И.В. Сб. работ 77-й научн. конф. студ. и аспир. БГУ, Минск, 15–18 мая 2020 г., в 3 ч., Минск.: БГУ, 2020, 377–380.
  31. Armarego W.L.F., Chai C.L.L. Purification of laboratory chemicals, 6th ed., Butterworth–Heinemann. 2009, 608.

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