Fomentarols A–D, sterols from the polypore macrofungus Fomes fomentarius

Some steroidal analogues embodying the hitherto unknown 13(148)-abeo skeleton have been synthesized by Fe(II)-induced rearrangement (tandem β-fission/reductive alkylation) of 14α-hydroperoxy-7-en-6-ones. The configurational assignment was made by thorough analysis of NMR spectra; the structure of one of the products was unambiguously assessed by X-ray single-crystal analysis.

Fe(II)‐Induced Fragmentation Reaction of γ‐Hydroperoxy‐α,β‐enones. Part 1. Synthesis of 13(14→8)‐abeo‐Steroids

A combination of chemical shift reagent effects, partially relaxed spectra, and carbon T1 measurements have been used to assign the chemical shifts of the carbons in seven different steroids which have served as intermediates in a synthesis of the steroid moulting hormone ecdysone. The assignments of ergosterol have been completed. It has been shown that the T1's are consistent with the molecular structures.

The carbon-13 spectra of steroids on the way to ecdysone

Le 2,25-dideoxy-α-ecdysone et le deoxyecdysone out ete prepares a partir de l'acetate d'ergosteryl. Dans l'essai biologique sur leCalliphora le dideoxy-α-ecdysone est la moitie moins actif que le β-ecdysone.

George P. Newsoroff

Papers

The synthesis of 23,24-14C-ecdysone.

An NMR Technique for Carbon-5 Configurations in 6-Keto-Δ -Steroids

Towards an ecdysone synthesis. 20β-acetoxy-5α-pregna-2, 7-dien-6-one