Further elution gave 4,19-oxido steroid 6 (0.013g, 17%), mp 208-210 °C (from ethyl acetate/hexane). Anal. Calcd. for C21H32O3: C 75.85; H 9.70. Found C 75.65; H 9.92;.dH (500 MHz) 0.614 (H3-18, s), 1.090 (H-9, ddd, J = 3.4, 10.4, 12.6), 1.416 (H-12a, m), 1.594 (H-2a, dd, 15.0, 4.5), 1.926 (H-2ß, m), 1.989 (H-12ß, dt, J = 12.5, 3.4), 2.008 (H-5, dd, J = 5.2, 12.7), 2.103 (H3-21, s), 2.524 (H-17, t, J = 9.0), 3.634 (H-19a, d, J = 8.0), 3.823 (H-4, d, J = 4.8), 3.875 (H- 19b, dd, 3J = 8.2, 4J = 1.8), 3.946 (H-3, br t, J = 4.3). dC (125 MHz) 13.6 (C-18), 22.8 (C-11), 23.5 (C-16), 24.2 (C-15), 29.6 (C-6), 32.3 (C-7), 31.5 (C-21), 30.8 (C-1), 35.5 (C-2), 36.4 (C-8), 39.2 (C-12), 44.0 (C-5), 44.4 (C-13), 45.6 (C-10), 47.7 (C-9), 55.8 (C-14), 63.8 (C-17), 69.0 (C- 3), 69.7 (C-19), 83.5 (C-4), 209.6 (C-20). m/z (EI): 332 (M+, 37), 317 (7), 314 (6), 302 (18), 287 (12), 274 (26), 273 (100), 230 (9).
Acknowledgments
We thank Universidad de Buenos Aires and CONICET for financial support. One of us (S.L.E.) also thanks Universidad de Buenos Aires for a fellowship.
References and Notes
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