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Synlett 2017; 28(01): 133-137
DOI: 10.1055/s-0036-1588072
DOI: 10.1055/s-0036-1588072
letter
Synthesis of Thia-Analogues of Calothrixin B Involving FeCl3-Mediated Domino Reaction
Authors
Further Information
Publication History
Received: 05 August 2016
Accepted after revision: 27 August 2016
Publication Date:
12 September 2016 (online)
Abstract
The total synthesis of thiacalothrixins, an isostere of the biologically important carbazoloquinone alkaloid calothrixin B, was achieved from ethyl benzo[b]thiophene-2-carboxylate. Alternatively, the multi-step synthesis of thiaisocalothrixins could be achieved from 3-methylbenzo[b]thiophene. A preliminary in vitro cytotoxicity evaluation of the synthesized thia analogues of calothrixins displayed promising potential against cancer cell cultures.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588072.
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- 18 Representative Procedure for the Preparation of Thiacalothrixin B (23a) To a solution of enamine 22a (300 mg, 0.8 mmol) in dry DMF (20 mL), FeCl3 (520 mg, 3.2 mmol) was added. The reaction mixture was refluxed for 3 h under N2 atmosphere. It was then poured over crushed ice (50 g) containing concd HCl (1 mL). The crude product was filtered and dried. It was then purified by flash column chromatography on silica gel (230–420 mesh, n-hexane–CH2Cl2 = 9:1 to 1:1) to afford thiacalothrixin B (23a) as a red-orange solid (160 mg, 65%); mp 260–262 °C. IR (film): 1651, 1519, 1258, 1092 cm–1. 1H NMR (300 MHz, CDCl3): δ = 9.81 (s, 1 H), 9.60 (d, J = 8.7 Hz, 1 H), 8.87 (d, J = 7.8 Hz, 1 H), 8.22 (d, J = 8.1 Hz, 1 H), 7.98 (d, J = 7.5 Hz, 1 H), 7.90 (t, J = 7.5 Hz, 1 H), 7.81 (t, J = 7.8 Hz, 1 H), 7.66–7.57 (m, 2 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 182.9, 180.3, 152.1, 148.7, 148.2, 142.4, 135.8, 133.6, 132.9, 132.1, 130.7, 130.4, 128.8, 127.7, 127.5, 127.3, 124.7, 123.0, 122.7 ppm. DEPT 135: δ = 148.2, 132.1, 130.7, 130.4, 128.8, 127.7, 127.5, 127.3, 123.0 ppm. HRMS (EI): m/z cacld for C19H9NO2S [M+]: 315.0354; found: 315.0354.