Total Synthesis of (±)-Xyloketal D and Model Studies towards the Total Synthesis of (-)-Xyloketal A

none 10.3987/COM-03-S(P)37

CLOCKSS Archive

5187

36453687

73640

20110922161649

10.13030

2024-06-24T16:37:53Z

2009-03-04T22:43:17Z

HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2004 62 1 Total Synthesis of (±)-Xyloketal D and Model Studies towards the Total Synthesis of (-)-Xyloketal A Peter D. Wilson Jeremy D. Pettigrew Jason A. Bexrud Rebecca P. Freeman 2004 445 COM-03-S(P)37 10.3987/COM-03-S(P)37 20110922161649 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-03-s%28p%2937 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-03-s%28p%2937 10.1021/jo015522r 1. Y. Lin, X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, L. L. P. Vrijmoed, E. B. G. Jones, K. Krohn, K. Steingröver, and F. Zsila, J. Org. Chem., 2001, 66, 6252. 10.1016/S0040-4020(02)00496-9 2. For a recent review on the chemistry of ortho-quinone methides, see: R. W. Van De Water and T. R. R. Pettus, Tetrahedron, 2002, 58, 5367. 10.1016/S0040-4020(02)01412-6 a) M. Anniyappan, D. Muralidharan, and P. T. Perumal, Tetrahedron, 2002, 58, 10301. b) J. S. Yadav, B. V. S. Reddy, M. Aurna, C. Venugopal, T. Ramalingam, S. K. Kumar, and A. C. Kunwar, J. Chem. Soc., Perkin Trans. 1, 2002, 165. 10.1021/ja00124a024 c) L. Diao, C. Yang, and P. Wan, J. Am. Chem. Soc., 1995, 117, 5369. 10.1139/v92-216 d) J. D. Chambers, J. Crawford, H. W. R. Williams, C. Dufresne, J. Scheigetz, M. A. Bernstein, and C. K. Lau, Can. J. Chem., 1992, 70, 1717. 10.1016/S0040-4039(01)01491-5 4. The corresponding Mannich base derived from 2,4-dihydroxyacetophenone, paraformaldehyde, and diethyl amine is a known compound, see: Y. Omura, Y. Taruno, Y. Irisa, M. Morimoto, H. Saimoto, and Y. Shigesasa, Tetrahedron Lett., 2001, 42, 7273. 10.1021/jo0006627 a) E. Modica, R. Zanaletti, M. Freccero, and M. Mella, J. Org. Chem., 2001, 66, 41. 10.1021/ja01522a052 b) P. D. Gardner, H. S. Rafsanjani, and L. Rand, J. Am. Chem. Soc., 1959, 81, 3364. 10.1016/S0040-4039(97)01071-X c) K. Nakantani, N. Higashida, and I. Saito, Tetrahedron Lett., 1997, 38, 5005. 10.1021/jo01090a008 Mannich bases of phloroglucinol have been prepared, see: a) F. F. Blicke and F. J. McCarty, J. Org. Chem., 1959, 24, 1061. b) A. P. Terent’ev, E. G. Rukhadze, and S. F. Zapuskalova, Probl. Org. Sint., 1965, 122 [Chem. Abstr., 1966, 64, 8065]. a) J. Colonge and R. Gelin, Bull. Soc. Chim. Fr., 1954, 799. 10.1039/jr9520002873 b) G. Eglinton, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc., 1952, 2873. 10.1016/S0040-4020(01)81460-5 a) B. B. Snider, A. J. Allentoff, and M. B. Walner, Tetrahedron, 1990, 46, 8031. 10.1002/jlac.19565980102 b) V. E. Buchta and H. Schlesinger, Liebigs Ann. Chem., 1955, 598, 1.