Synthesis, Table of Contents Synthesis 2023; 55(04): 663-669DOI: 10.1055/a-1947-6049 paper Synthesis of (±)-5-epi-Vetiverianine A via an Oxidative Cyclization Approach Eiji Nagata , Hisaaki Sakate , Takaharu Okada , Shinya Adachi , Shogo Kamo , Akinobu Matsuzawa , Kazuyuki Sugita ∗ Recommend Article Abstract Buy Article All articles of this category Abstract In this article, we report the synthesis of (±)-5-epi-vetiverianine A. The key reactions, including a rhodium-catalyzed coupling reaction and an oxidative phenolic cyclization, allow for efficient and stereoselective access to (±)-5-epi-vetiverianine A in 11 steps, and in 20% overall yield. The stereochemistry is confirmed by NOE studies. Key words Key wordssynthetic study - vetiverianine A - 5-epi-vetiverianine A - oxidative cyclization - Rh-catalyzed coupling Full Text References References 1 Belhassen E, Filippi JJ, Brévard H, Joulain D, Baldovini N. Flavour Fragrance J. 2015; 30: 26 2 Matsuo Y, Maeda S, Ohba C, Fukaya H, Mimaki Y. J. Nat. Prod. 2016; 79: 2175 3a Gupta S, Dwivedi GR, Darokar MP, Srivastava SK. Med. Chem. Res. 2012; 21: 1283 3b Manosroi J, Dhumtanom P, Manosroi A. Cancer Lett. 2006; 235: 114 4a Rihn S, Retailleau P, De Nicola A, Ulrich G, Ziessel R. J. Org. Chem. 2012; 77: 8851 4b Kuwabara M, Matsuo A, Kamo S, Matsuzawa A, Sugita K. Synthesis 2021; 53: 2092 5 Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508 6a Hayashi T. Synlett 2001; 879 6b Edwards HJ, Hargrave JD, Penrose SD, Frost CG. Chem. Soc. Rev. 2010; 39: 2093 6c Matsuo R, Watanabe A, Kamo S, Matsuzawa A, Sugita K. Org. Chem. Front. 2021; 8: 6063 7a Kerrigan NJ, Hutchison PC, Heightman TD, Procter DJ. Chem. Commun. 2003; 1402 7b Kerrigan NJ, Hutchison PC, Heightman TD, Procter DJ. Org. Biomol. Chem. 2004; 2: 2476 8 Shafi MS, Chou J, Kataoka K, Nokami J. Org. Lett. 2005; 7: 2957 9a Dai M, Danishefsky SJ. Heterocycles 2009; 77: 157 9b Wei X, Xiao M, Xie Z. Org. Lett. 2014; 16: 2784 10a Other diastereomers were removed during the purification process. 10b Burn D, Cooley G, Ellis B, Heal AR, Petrov V. Tetrahedron 1963; 19: 1757 10c Mori K, Mori H, Yanai M. Tetrahedron 1986; 42: 291 11a Singh V, Sahu BC, Bansal V, Mobin SM. Org. Biomol. Chem. 2010; 8: 4472 11b Vidrna L, Cerny I, Pouzara V, Borovska J, Vyklicky V, Vyklicky LJr, Chodounska H. Steroids 2011; 76: 1043 12a Imanishi T, Ninbari F, Yamashita M, Iwata C. Chem. Pharm. Bull. 1986; 34: 2268 12b Iwata C, Takemoto Y, Doi M, Imanishi T. J. Org. Chem. 1988; 53: 1623 13a Jiang CH, Bhattacharyya A, Sha CK. Org. Lett. 2007; 9: 3241 13b Lee H.-Y, Sha C.-K. J. Org. Chem. 2012; 77: 598 14 In this reaction, other isomers and the compounds bearing a benzyl group were also produced. They were removed by column chromatography. 15a Crabtree RH, Felkin H, Morris GE. J. Organomet. Chem. 1977; 141: 205 15b Davis MW, Crabtree RH. J. Org. Chem. 1986; 51: 2655 15c Kraus GA, Shi J. J. Org. Chem. 1991; 56: 4147 15d Tamura K, Nakazaki A, Kobayashi S. Synlett 2009; 2449 16a D’Incan E, Loupy A, Maia A. Tetrahedron Lett. 1981; 22: 941 16b Ngo K.-S, Brown GD. Tetrahedron 1999; 55: 15109 17a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155 17b Meyer SD, Schreiber SL. J. Org. Chem. 1994; 59: 7549 Supplementary Material Supplementary Material Supporting Information
