80680-87-1

Upstream product

• 80680-88-2 Acetic acid (2S,4aS,5S,6R,8aR)-4a-methyl-6-[(S)-2-methyl-3-(5-oxo-2,5-dihydro-furan-3-yl)-cyclopent-1-enyl]-5-(2-oxo-ethyl)-decahydro-naphthalen-2-yl ester 
• 2842-86-6 3β-Acetoxy-14-hydroxy-12-oxo-5β,14β-card-20(22)-enolid 
• 80680-85-9 3β-Acetoxy-12-oxo-5β,14α-card-20(22)-enolid 

Relevant academic research and scientific papers

Elimination Reactions and Rearrangement of 14β-Hydroxy-12-sulfonyloxy Steroids.

Elimination of 12α- or 12β-(methylsulfonyloxy)-14β-hydroxy steroids proceeds under rearrangement of the steroid nucleus.From the 12α-sulfonyloxy compounds of 19 the (12βH)-14(13->12)abeo-13(18)-ene steroid 21 is obtained, whereas the 14β-hydroxy-(12βH)-17(13->12)abeo-13(18)ene compounds 14, 20 result from the 12β-methylsulfonyloxy derivatives of the steroids 13, 18.Structures were determined by means of 2D-NMR analyses and decoupling experiments.The theoretical explanation of this rearrangement leads to the possibility of an elimination of the 12α-methylsulfonyloxy group to yield the Δ11-alkene (28).This is possible by steric fixation of the migrating C-atoms at positions 14 and 17 in the 20,14β-lactone (26, 27).

14β-HYDROXY STEROIDS-III. SYNTHESIS OF DIGOXIGENIN FROM DEOXYCHOLIC ACID

A new synthetic approach to cardenolides is discussed which employs singlet oxygen addition to dienol ethers and an intramolecular Prins reaction.