Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 21
467
Views
2
CrossRef citations to date
0
Altmetric
Articles

Chiron approach towards optically pure γ-valerolactone from alanine

, , , &
Pages 2801-2808 | Received 21 Mar 2018, Published online: 10 Nov 2018

References

  • (a) Mandrioli, R.; Mercolini, L.; Saracino, M. A.; Raggi, M. A. Curr. Med. Chem. 2012, 19, 1846–1863. (b) Ghosh, A. K.; Swanson, L. J. Org. Chem. 2003, 68, 9823–9826. (c) Lipshutz, B. H.; Lower, A.; Kucejko, R. J.; Noson, K. Org. Lett. 2006, 8, 2969–2972. (d) Stangeland, E. L.; Sammakia, T. J. Org. Chem. 2004, 69, 2381–2385. (e) Hilbon, J. W.; Lu, Z. H.; Jurgens, A. R.; Fang, Q. K.; Byers, P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2001, 42, 8919–8921. doi:10.2174/092986712800099749
  • (a) Tukacs, J. M.; Fridrich, B.; Dibó, G.; Székelya, E.; Mika, L. T. Green Chem. 2015, 17, 5189–5195. (b) Datrika, R.; Kallam, S. R.; Khobare, S. R.; Gajare, V. S.; Kommi, M.; Mohan, H. R.; Vidavalur, S.; Pratap, T. V. Tetrahedron: Asymmetry. 2016, 27, 603–607. (c) Datrika, R.; Kallam, S. R.; Gajare, V.; Khobare, S.; Rama, V. S.; Kommi, M.; Hindupur, R. M.; Vidavulur, S.; Tadikonda, P. V. Synthesis of (+)-Patulolide C Using R -(+)-γ-Valerolactone as a Chiral Synthon. Chem. Select. 2017, 2, 5828–5831. doi:10.1039/C5GC01099C
  • (a) Resul, B.; Stjernschantz, J.; No, K.; Liljebris, C.; Selen, G.; Astin, M.; Karlsson, M.; Bito, L. Z. J. Med. Chem. 1993, 36, 243–248. (b) Poth, D.; Peram, P. S.; Vences, M.; Schulz, S. J. Nat. Prod. 2013, 76, 1548–1558. (c) Patel, P.; Lee, G.-J.; Kim, S.; Grant, G. E.; Powell, W. S.; Rokach, J. J. Org. Chem. 2008, 73, 7213–7218. (d) Poth, D.; Wollenberg, K. C.; Vences, M.; Schulz, S. Angew. Chem. Int. Ed. 2012, 51, 2187–2190. doi:10.1021/jm00054a008
  • Ramachandran, P. V.; Pitre, S.; Brown, H. C. Selective Reductions. 59. Effective Intramolecular Asymmetric Reductions of Alpha-, Beta-, and Gamma-Keto Acids with Diisopinocampheylborane and Intermolecular Asymmetric Reductions of the Corresponding Esters with B-Chlorodiisopinocampheylborane. J. Org. Chem. 2002, 67, 5315–5319. doi:10.1021/jo025594y
  • Starodubtseva, E. V.; Turova, O. V.; Vinogradov, M. G.; Gorshkova, L. S.; Ferapontov, V. A.; Struchkova, M. I. A Convenient Route to Chiral γ-Lactones via Asymmetric Hydrogenation of γ-Ketoesters Using the RuCl3–BINAP–HCl Catalytic System. Tetrahedron. 2008, 64, 11713–11717. doi:10.1016/j.tet.2008.10.012
  • (a) Sugai, T.; Hamada, K.; Akeboshi, T.; Ikeda, H.; Ohta, H. Synlett 1997, 8, 983–985. (b) Forzato, C.; Gandolfi, R.; Molinari, F.; Nitti, P.; Pitacco, G.; Valentin, E. Tetrahedron Asymmetry. 2001, 12, 1039–1046. (c) Nanduri, V. B.; Hanson, R. L.; Goswami, A.; Wasylyk, J. M.; LaPorte, T. L.; Katipally, K.; Chung, H. J.; Patel, R. N. Enzyme Microb. Technol. 2011, 28, 632–636.
  • (a) Jacobs, H.; Berryman, K.; Jones, J.; Gopalan, A. Synth. Commun. 1990, 7, 999–1010. (b) Tsuboi, S.; Sakamoto, J.; Kawano, T.; Utaka, M.; Takeda, A. J. Org. Chem. 1991, 56, 7177–7179. (c) White, J. D.; Somers, T. C.; Reddy, G. N. J. Org. Chem. 1992, 57, 4991–4998. (d) Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry. 1995, 6, 157–164. (e) Nair, V.; Prahakaran, J.; George, T. G. Tetrahedron. 1997, 53, 15061–15068. (f) Rodriguez, A. D.; Borzecka, W.; Lavandera, I.; Gotor, V. ACS Catal. 2014, 4, 386–393.
  • Aitken, R.; Meehan, A.; Power, L. Synthesis of (R)-Lactic Acid and (2R,5R)-2-Tert-Butyl-5-Methyl-1,3-Dioxolan-4-One. Synthesis. 2015, 47, 1557–1559. doi:10.1055/s-0034-1380511
  • Corey, E. J.; Venkateswarlu, A. Protection of Hydroxyl Groups as Tert-Butyldimethylsilyl Derivatives. J. Am. Chem. Soc. 1972, 94, 6190–6191. doi:10.1021/ja00772a043
  • Wittig, G.; Schoellkopf, U. Methylenecyclohexane. Org. Synth. 1960, 40, 66.
  • Wang, S.-Y.; Song, P.; Chin, Y.; Jin.; Loh, T.-P. A General Strategy for the Introduction of Stereogenic Centers Bearing a Methyl Group: Total Synthesis of Sex Pheromones. Chem. Asian J. 2011, 6, 385–388.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.