Stickstoffhaltige Steroide. XXIII. 16‐Azido‐ und 16‐Amino‐D‐Homo‐Steroide

Ponsold, K.; Schönecker, Bruno; Rosenberger, H.; Prousa, R.; Müller, Bettina

doi:10.1002/prac.19693110608

Cited by 5 publications

(1 citation statement)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The pregnene derivative 25 was also synthesized by acid-catalyzed opening of the corresponding α-epoxide. It is worthy of note that, under exactly the same reaction conditions, Ponsold described the formation of a derivative with ring D rearranged to a six-membered hydroxy azide (3β-acetoxy-16β-azido-17α-hydroxy-17β-methyl- d -homoandrost-5-en-17a-one) as the sole product but, in our hands, the hitherto unknown five-membered hydroxy azide 25 (77%) is the principal product, the six-membered azide being formed in only 9% yield.…”

Section: Resultssupporting

confidence: 52%

Synthesis of Highly Functionalized Chiral Nitriles by Radical Fragmentation of β-Hydroxy Azides. Convenient Transformation of Aldononitriles into 1,4- and 1,5-Iminoalditols

et al. 2004

View full text Add to dashboard Cite

The synthesis of highly functionalized nitriles by an alkoxyl radical fragmentation of cyclic beta-hydroxy azides is described. The alkoxyl radicals were generated by reaction of the alcohols with (diacetoxyiodo)benzene and iodine under mild conditions compatible with the presence of sensitive substituents and the protective groups most frequently used in carbohydrate chemistry. To explore the scope and limitations of this methodology, experiments were carried out using a variety of beta-hydroxy azides of the carbohydrate (1-6, 33, and 41), monoterpenoid (21 and 22), and steroid (23-25) families of natural products. Of special interest are the aldopentonitriles (15-18, 34, and 42) and aldotetrononitriles (19 and 20) synthesized from the corresponding 2-azido-2-deoxycarbohydrates. To demonstrate the versatility of these aldononitriles as chiral synthons, 1,4-imino-1-deoxysugar (37) and 1,5-imino-1-deoxysugar (43) analogues of the polyhydroxypyrrolidine and -piperidine types were prepared.

show abstract

Section: Resultssupporting

confidence: 52%