Collect. Czech. Chem. Commun. 1998, 63, 655-661

N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide

Barbora Slavíková, Alexander Kasal and Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


3β-Hydroxyandrost-5-en-17-one (1) was converted into 17β-(N-methylamino)androst-5-en-3β-ol (4). In the corresponding N-benzamide 5, structural features characteristic of brassinolide were produced in a standard way, i.e. via 3α,5α-cyclo derivatives 7 and 8, ∆2-olefin 9 and 2α,3α-diol 10. Baeyer-Villiger oxidation yielded two products: 2α,3α-dihydroxy-17β-N-(methylbenzamido)-7-oxa-7a-homo-5α-androstan-6-one (11) and 2α,3α-dihydroxy-17β-(N-methylbenzamido)-6-oxa-7a-homo-5α-androstan-7-one (12).

Keywords: Steroids; Brassinosteroids; Leuckart reaction; Aza steroids; 1H NMR spectroscopy; Baeyer–Villiger oxidation; N-Methylmorpholine N-oxide.