Catharsitoxins from the Chinese remedy qiung laug

Author:

Suenaga Kiyotake,Shimogawa Hiroki,Nakagawa Satoru,Uemura Daisuke

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference9 articles.

1. Terada, B. J. Orient. Med. 1935, 22, 58; Chem. Abstr. 1937, 31, 8023.

2. Radical cyclisation onto imidazoles and benzimidazoles

3. Compound 2: 1H NMR (800 MHz, CD3OD containing one drop of TFA) δ 3.92 (dd, J=5.9, 5.9 Hz, 2H), 2.96 (dd, J=6.3, 6.3 Hz, 2H), 2.66 (q, J=7.6 Hz, 2H), 2.24 (s, 3H), 2.10 (m, 2H), 2.00 (m, 2H), 1.23 (t, J=7.6 Hz, 3H); HRFABMS m/z 165.1415, calcd for C10H17N2 (M+H)+ 165.1392.Compound 3: 1H NMR (800 MHz, CD3OD containing one drop of TFA) δ 7.12 (s, 1H), 4.09 (dd, J=5.9, 5.9 Hz, 2H), 2.97 (dd, J=6.3, 6.3 Hz, 2H), 2.97 (m, 1H), 2.09 (m, 2H), 2.01 (m, 2H), 1.31 (d, J=7.2 Hz, 6H); HRFABMS m/z 165.1395, calcd for C10H17N2 (M+H)+ 165.1392.Compound 5: 1H NMR (800 MHz, CD3OD containing one drop of TFA) δ 7.79 (s, 1H), 7.70 (dd, J=8.0, 1.4 Hz, 2H), 7.53 (dd, J=7.6, 7.6 Hz, 2H), 7.47 (t, J=7.6 Hz, 1H), 3.19 (m, 1H), 1.86 (m, 2H), 1.47 (d, J=9.6 Hz, 3H), 0.96 (t, J=7.2 Hz, 3H); HRFABMS m/z 201.1412, calcd for C13H17N2 (M+H)+ 201.1392. This compound was found to be racemic by chiral HPLC analysis.Compound 6: 1H NMR (800 MHz, CD3OD containing one drop of TFA) δ 7.79 (s, 1H), 3.02 (m, 1H), 2.79 (d, J=6.3 Hz, 1H), 2.10 (m, 1H), 1.32 (d, J=7.4 Hz, 6H), 0.98 (d, J=6.5 Hz, 6H); HRFABMS m/z 167.1553, calcd for C10H18N2 (M+H)+ 167.1548.

4. Ruthenium-catalyzed hydration of nitriles and transformation of δ-ketonitriles to ene-lactams: total synthesis of (−)-pumiliotoxin C

5. A Convenient Synthesis of 3-Chloro-2-alkanones

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