A Diels-Alder approach for the synthesis of highly functionalized benzo-annulated indane-based α-amino acid derivatives via a sultine intermediate

Tetrahedron Letters

Volumn 45, Issue 14, 2004, Pages 2931-2934

  Kotha, Sambasivarao ^a   Ghosh, Arun Kumar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Amino acid; DDQ oxidation; Diels Alder cycloaddition; Fullerene; Sultine

Indexed keywords

ALKADIENE; AMINO ACID DERIVATIVE; BENZENE DERIVATIVE; FULLERENE; INDAN DERIVATIVE;

ARTICLE; COMBINATORIAL CHEMISTRY; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 1642399542     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.060     Document Type: Article

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37. 4. The solvent was evaporated and the crude product was charged on a silica gel column. Elution of the column with ethyl acetate/petroleum ether gave the desired product.
38. 3) spectral data of all new compounds are given here. 7 δ=1.25 (t, J=7.1 Hz, 3H), 1.96 (s, 3H), 3.25 (d, J=16.8 Hz, 2H), 3.61 (d, J=16.8 Hz, 2H), 4.22 (q, J=7.1 Hz, 2H), 4.65 (s, 4H), 6.03 (s, 1H), 7.21 (s, 2H). 9 δ=1.24 (t, J=7.3 Hz, 3H), 1.95 (s, 3H), 3.30 (d, J=16.8 Hz, 2H), 3.53 (d, J=15.4 Hz, 1H), 3.62 (d, J=16.8 Hz, 2H), 4. 22 (q, J=7.3 Hz, 2H), 4.40 (d, J=15.3 Hz, 1H), 4.92 (d, J=13.5 Hz, 1H), 5.27 (d, J=13.2 Hz, 1H), 6.11 (s, 1H), 7.12 (s, 1H), 7.14 (s, 1H). 10 δ=1.24 (t, J=7.2 Hz, 3H), 1.95 (s, 3H), 3.27 (d, J=16.8 Hz, 2H), 3.54 (d, J=15.3 Hz, 1H), 3.63 (d, J=16.8 Hz, 2H), 4.21 (q, J=7.2 Hz, 2H), 4.31 (d, J=15.2 Hz, 1H), 4.92 (d, J=13.5 Hz, 1H), 5.23 (d, J=13.5 Hz, 1H), 6.15 (s, 1H), 7.07 (s, 1H), 7.10 (s, 1H). 12 δ=1.23 (t, J=6.9 Hz, 3H), 1.95 (s, 3H), 3.49 (d, J=16.8 Hz, 2H), 3.71 (d, J=16.8 Hz, 2H), 3.94 (s, 6H), 4.21 (q, J=6.9 Hz, 2H), 6.11 (s, 1H), 7.67 (s, 2H), 8.11 (s, 2H). 13 δ=1.25 (t, J=7.3 Hz, 3H), 1.95 (s, 3H), 3.49 (dd, J=16.8, 5.1 Hz, 2H), 3.71 (dd, J=17.2, 7.1 Hz, 2H), 3.97 (s, 3H), 4.23 (q, J=7.3 Hz, 2H), 6.0 (s, 1H), 7.69 (s, 1H), 7.75 (s, 1H), 7.8 (d, J=8.4 Hz, 1H), 8.0 (dd, J=8.4, 1.5 Hz, 1H), 8.53 (s, 1H). 14 δ=1.23 (t, J=7.1 Hz, 3H), 1.98 (s, 3H), 3.55 (d, J=17.4 Hz, 2H), 3.77 (d, J=17.4 Hz, 2H), 4.23 (q, J=7.1 Hz, 2H), 6.16 (s, 1H), 7.04 (s, 2H), 7.85 (s, 2H), 8.52 (s, 2H). 15 δ=1.25 (t, J=7.3 Hz, 3H), 1.99 (s, 3H), 3.56 (d, J=17.2 Hz, 2H), 3.78 (d, J=17.2 Hz, 2H), 4.24 (q, J=7.2 Hz, 2H), 6.16 (s, 1H), 7.81-7.85 (m, 2H), 7.88 (s, 2H), 8.37-8.41 (m, 2H), 8.75 (s, 2H). 16 δ=1.25 (t, J=7.3 Hz, 3H), 1.99 (s, 3H), 3.57 (d, J=17.2 Hz, 2H), 3.79 (d, J=17.2 Hz, 2H), 4.24 (q, J=7.2 Hz, 2H), 6.11 (s, 1H), 7.70-7.73 (m, 2H), 7.92 (s, 2H), 8.12-8.15 (m, 2H), 8.86 (s, 2H), 8.94 (s, 2H). 17 δ=1.25 (br s, 3H), 2.03 (s, 3H), 3.47 (d, J=16. 0 Hz, 2H), 3.79 (d, J=16.0 Hz, 2H), 4.26 (q, J=7.3 Hz, 2H), 4.40 (d, J=14.1 Hz, 2H), 4.78 (d, J=14.1 Hz, 2H,), 6.14 (s, 1H), 7.51 (s, 1H).