A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene

Author:

Leonard John,Hague Andrew B,Jones Martin F

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

1. a) Szántay, C.; Honty, K. Monoterpenoid Indole Alkaloids (Supplememnt to Vol. 25 Part 4). In The Chemistry of Heterocyclic Compounds; Saxton, J.E., Ed.; Wiley, 1994; p. 161; b) Brown, R.T.,Monoterpenoid Indole Alkaloids; In, The Chemistry of Heterocyclic Compounds: Indoles, Part 4; Saxton, J.E., Ed.; Wiley, 1983; p. 145; c) Szántay, C., Blaskó, G., Honty, K. and Dörnyei, G., in The Alkaloids, Brossi, A., Ed.; Academic Press, New York, 1986; vol. 27, ch. 2; d) Leonard, J. The Alkaloids. In The Chemistry of Natural Products, Thomson, R.H., Ed.; Chapman and Hall, 1993; pp. 218–258:

2. Chirality in α- and β-adrenoceptor agonists and antagonists

3. a) Martin, S.F.; Williamson, S.A.; Gist, R.P.; Smith, K.M. J. Org. Chem., 1983, 48, 5170; b) Martin, S.F.; Rueger, H.; Williamson, S.A.; Grzejszczak, S. J. Am. Chem. Soc., 1987, 109, 6124; c) Martin, S.F.; Benage, B.; Hunter, J.E. J. Am. Chem. Soc., 1988, 110, 5925; d) Martin, S.F.; Benage, B.; Williamson, S.A.; Brown, S.P. Tetrahedron, 1986, 42, 2903; e) Yamaguchi, R.; Otsuji, A.; Utimoto, K. J. Am. Chem. Soc., 1988, 110, 2186–2187; f) Yamaguchi, R.; Hamasaki, T.; Utimoto, K.; Kozima, S.; Takaya, H.; Chem. Lett., 1990, 2161–2164; g) Meyers, A.I.; Highsmith, T.K.; Buonora, P.T. J. Org. Chem., 1991, 56, 2960–2964.

4. Unified strategy for synthesis of indole and 2-oxindole alkaloids

5. For examples of related Diels-Alder reactions, see: a) Martin, S.F.; Chou, T.S.; Tu, C.Y. Tetrahedron Lett., 1979, 19, 3823; b) Martin, S.F.; Tu, C.Y.; Chou, T.S. J. Am. Chem. Soc., 1980, 102, 5274–5279; c) Lathbury, D.C.; Parsons, P.J.; Pinto, I.; Chem. Commun., 1988, 81; d) Levy, J.; Laronze, J-Y.; Sapi, J. Tetrahedron Lett., 1988, 29, 3303–3306; e) Martin, S.F.; Rein, T.; Liao, Y. Tetrahedron Lett., 1991, 32, 6481; f) Leonard, J.; Fearnley, S.P.; Finlay, M.R.; Knight J.A.; Wong, G. J. Chem. Soc. Perkin Trans 1, 1994, 2359–2361.

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