Tetrahedron Letters p. 4295 - 4298 (1989)
Update date:2022-08-10
Topics:
Kocovsky, Pavel
Stieborova, Irena
A 16-step synthesis of strophanthidin (3) from a commercially available steroid 4 is described.Salient features of this approach are the selective reduction of the dienone system in 7 to give 8 and a one-pot introduction of 5β- and 14β-hydroxyls by addition of HOBr (14 -> 15).The stereo- and regioselectivity of the HOBr addition to the 5,6-double bond is controlled by 19-formyloxy group.
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Doi:10.1002/cmdc.201700543
(2018)Doi:10.1002/anie.201102320
(2011)Doi:10.1039/c5cc00750j
(2015)Doi:10.1039/c7nj03372a
(2017)Doi:10.1055/s-1991-26630
(1991)Doi:10.1021/ja01383a501
(1929)
