Synthetic Approach to an Analog of Plakoridine-A using Malate Enolate-Imine Condensation

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Marine Matural Products, Diversity and Biosynthesis v.167 Topics in Cur-rent Chemistry Gerwick, W. H.;Nagle, D. G.;Proteau, P. J.;Scheuer, P. J.(ed.)
Tetrahedron no.51 Takeuchi, S.;Kikuchi, T.;Tsukamoto, S.;Ishibashi, M.;Kobayashi, J.
J. Org. Chem. no.59 Takeu-chi, S.;Ishibashi, M.;Kobayashi, J.
Tetrahedron Lett. no.36 Stafford, J. A.
Tetrahedron Lett. no.41 Ma, D.;Sun, H.
Tetrahedron Lett. no.36 Ha, D.-C.; Yun, K.-S.; Park, H.-S.; Choung, W.-K.; Kwon, Y.-E.
Chem. Rev. no.89 Hart, D. J.;Ha, D.-C.
Tetrahedron no.41 For review, see:Cava, M. P.;Levinson, M. I.
Helv. Chim. Acta no.54 Roth, M.;Dubs, P.;Gotsch, E.;Eschenmoser, A.
Quart. Rev. no.24 Eschenmoser, A.
J. Org. Chem. no.42 Cardillo, G.;Shimizu, M.
Selected 1 H NMR (CDCl3, 300 MHz) data. 4: d 7.18 (d, 2H, J = 9 Hz), 7.03 (m, 5H), 6.93 (d, 2H, J = 9 Hz), 5.87 (s, 1H), 4.94 (s, 1H), 3.84 (s, 3H), 3.62 (m, 2H), 3.50 (m,1H), 2.70 (m, 1H), 2.50-2.42 (m, 2H), 2.09 (t, 2H, J = 6 Hz), 2.05 (m, 2H), 1.25 (m, 28H), 1.14 (m, 42H), 0.88 (t, 3H, J = 6.3 Hz). 12: d 7.22 (m, 5H), 7.06 (d, 2H, J = 9 Hz), 6.94 (d, 2H, J = 9 Hz), 4.62 (s, 1H), 4.05 (m, 1H), 3.82 (s, 3H), 3.75 (m, 2H), 2.60 (m, 2H), 2.45 (m, 1H), 2.10-1.90 (m, 2H), 1.13 (m, 42H).