Synlett 2013; 24(16): 2102-2106
DOI: 10.1055/s-0033-1339655
letter
© Georg Thieme Verlag Stuttgart · New York

Transition Metals in Organic Synthesis, Part 111:[1] First Total Synthesis and Structural Revision of Antipathine A

Andreas Berndt
Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Fax: +49(351)46337030   Email: hans-joachim.knoelker@tu-dresden.de
,
Margit Gruner
Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Fax: +49(351)46337030   Email: hans-joachim.knoelker@tu-dresden.de
,
Arndt W. Schmidt
Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Fax: +49(351)46337030   Email: hans-joachim.knoelker@tu-dresden.de
,
Hans-Joachim Knölker*
Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Fax: +49(351)46337030   Email: hans-joachim.knoelker@tu-dresden.de
› Author Affiliations
Further Information

Publication History

Received: 18 July 2013

Accepted: 01 August 2013

Publication Date:
21 August 2013 (online)


Abstract

We describe the first total synthesis of antipathine A and a revision of the original structural assignment.

Supporting Information

 
  • References and Notes

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  • 13 Spectroscopic Data for Antipathine A {1,3-Dimethyl-1H-pyrimido[5,4-b]carbazole-2,4(3H,6H)-dione} (2) Yellow solid; mp 342–344 °C. UV (MeOH): λ = 219, 260, 318 (sh), 327, 383, 398 nm. Fluorescence (MeOH): λex = 260 nm, λem = 448 nm. IR (ATR): ν = 3263, 3028, 2921, 2846, 1771, 1735, 1717, 1686, 1626, 1559, 1540, 1518, 1456, 1432, 1377, 1333, 1307, 1241, 1191, 1146, 1098, 1067, 1017, 965, 856, 834, 765, 742, 723, 706, 640 cm–1. 1H NMR (500 MHz, C5D5N): δ = 3.57 (s, 3 H), 3.66 (s, 3 H), 7.35 (t, J = 7.4 Hz, 1 H), 7.59 (t, J = 7.6 Hz, 1 H), 7.66 (d, J = 8.2 Hz, 1 H), 8.14 (s, 1 H), 8.41 (d, J = 7.8 Hz, 1 H), 8.65 (s, 1 H), 12.72 (br s, 1 H). 13C NMR (125 MHz, C5D5N): δ = 28.51 (CH3), 31.03 (CH3), 104.87 (CH), 110.19 (CH), 112.03 (CH), 114.50 (C), 119.62 (CH), 122.18 (CH), 122.91 (C), 128.46 (CH), 129.76 (C), 133.94 (C), 136.74 (C), 143.60 (C), 151.09 (C=O), 162.71 (C=O). MS (70 eV): m/z (%) = 279 (100) [M+], 222 (10), 221 (5), 194 (18), 193 (36), 192 (5), 167 (10), 166 (12), 139 (7). HRMS: m/z calcd for C16H13N3O2 [M+]: 279.1008; found: 279.1001.

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