Lead tetraacetate-iodine oxidation of 23-spirostanols

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1929-1932

  Jastrzȩbska, Izabella ^a   Morzycki, Jacek W ^a   Trochimowicz, Urszula ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Lead tetraacetate; Oxidation; Spirostanes; Steroids

Indexed keywords

CARBON TETRACHLORIDE; IODINE; SPIROSTAN DERIVATIVE; TETRAETHYLLEAD;

ARTICLE; LOW TEMPERATURE; OXIDATION; REACTION ANALYSIS;

EID: 1242271364     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.146     Document Type: Article

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26. 3), 0.99 (s, 3H, 18-H), 0.93 (s, 3H, 19-H); MS-ESI (in MeOH, m/z ): 671 (M+MeOH+Na, 100%), 639 (M+Na, 24%).
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28. 3): 5.37 (m, 1H, 6-H), 5.13 (m, 1H, 16α-H), 4.61 (m, 1H, 3α-H), 2.49 (d, J=4.1 Hz, 1H, 17α-H), 2.04 (s, 3H, AcO), 1.90 (s, 3H, 21-H), 1.03 (s, 3H, 19-H), 0.84 (s, 3H, 18-H); MS-EI ( m/z ): 362 and 360 (M-AcOH, 38% and 100%), 347 (10%), 345 (30%).
29. 3): 5.37 (m, 1H, 6-H), 5.19 (m, 1H, 16α-H), 4.74 (d, J=13.0 Hz, 1H, 21-H), 4.60 (m, 1H, 3α-H), 4.51 (d, J=13.0 Hz, 1H, 21-H), 2.54 (d, J=5.8 Hz, 1H, 17α-H), 2.17 (s, 3H, AcO), 2.04 (s, 3H, AcO), 1.03 (s, 3H, 19-H), 0.88 (s, 3H, 18-H); MS-EI ( m/z ): 442 (M-HCl, 7%), 420 and 418 (M-AcOH, 26% and 74%), 403 (14%), 324 (78%).