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under nitrogen to afford a pale brown solution. The reaction mix-
ture was stirred for 12 h at room temperature and additional HATU
(125 mg, 0.33 mmol) was added. Stirring was continued for 24 h at
room temperature, and the solvent was removed under reduced
pressure. Flash column chromatography purification (CH2Cl2/
MeOH 18:1) afforded the cyclopeptide–furostane conjugate 18
(111 mg, 61%) as a pale yellow solid. Mp (from acetone): 255–
257 ꢀC. 1H NMR (CDCl3): d¼0.80 (s, 3H); 0.82 (s, 3H); 0.88, 0.90, 0.92
(3ꢁd, 9H, 2ꢁCH3þ3H-27); 0.96 (d, 3H, J¼6.8 Hz, H-21); 2.01 (s, 3H,
Ac); 2.72 (dd, 1H, J¼15.0/7.1 Hz); 2.78 (dd, 1H, J¼14.9/7.2 Hz); 3.33
(m, 1H, H-22a); 3.90 (m, 1H); 3.98 (m, 1H); 4.22 (dd, 1H, J¼14.3/
6.8 Hz); 4.29 (dd, 1H, J¼14.4/6.7 Hz); 4.31–4.58 (m, 6H); 5.54 (m,
1H, NH); 5.73 (m, 1H, NH); 6.12 (d, 1H, J¼7.9 Hz, NH); 7.37–7.71 (m,
5H, Bz). 13C NMR (CDCl3): d¼16.8, 17.4, 17.8, 18.2, 18.6, 18.7, 20.8,
21.0, 30.3, 30.5, 31.8, 32.6, 32.9, 34.7, 35.5, 36.4, 37.1, 37.8, 38.8, 39.4,
39.8, 40.4, 42.3, 45.0, 46.2, 50.3, 51.6, 54.8, 67.7, 68.8, 70.2, 77.4, 90.3,
125.4,128.8,129.8,130.4,130.7,133.5,168.1,169.7,170.9,171.2,171.3,
172.4. HRMS (ESI-FT-ICR) m/z: 854.5036 [MþNa]þ; calcd for
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Acknowledgements
We are grateful to the Leibniz Institute of Plant Biochemistry,
Halle/Saale, Germany, for providing the HRMS measurements and
for the generous gift of some chemicals. We also thank the Institute
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of Materials, Universidad Nacional Autonoma de Mexico, for some
NMR measurements.
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