10211-58-2

Upstream product

• 53-03-2 Prednison 
• 3607-68-9 17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione 
• 26341-55-9 prednisone-BMD 
• 143418-92-2 4,5-seco-17α,20;20,21-bismethylenedioxypregnane-3,5,11-trione 
• 89376-69-2 3-hydroxy-9,10-seco-17α,20;20,21-bismethylenedioxypregna-1,(10),2,4-trien-11-one 
• 143418-91-1 10,11-cyclo-4,5-seco-17α,20;20,21-bismethylenedioxypregn-3(11)-en-5-one 
• 143418-89-7 C₂₃H₃₄O₆ 
• 116202-10-9 des-A,B-11-oxo-17α,20;20,21-bismethylenedioxypregnane-8α-propionic acid 
• 50-00-0 formaldehyd 
• 50-23-7 cortisol 

Downstream Products

• 6818-44-6 4-((3R,5S,7R,10S,12S,13R)-3,7,12-Triacetoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 

Relevant academic research and scientific papers

METHODS FOR PREPARING SYNTHETIC BILE ACIDS AND COMPOSITIONS COMPRISING THE SAME

This invention relates generally to methods for preparing certain bile acids from non-mammalian sourced starting materials as well as to synthetic bile acids and compositions comprising such acids wherein the acids are characterized by a different C14 population than naturally occurring bile acids as well as being free from any mammalian pathogens. This invention is also directed to the synthesis of intermediates useful in the synthesis of such bile acids. Accordingly, the C ring of the steroidal scaffold is oxidized to provide a synthetic route and intermediates to DCA. This invention also provides synthetic methods for preparing deoxycholic acid or a salt thereof starting from aromatic steroids such as estrogen, equilenin, and derivatives thereof. This invention is also directed to intermediates such as 12-oxo or delta-9,11-ene steroids as well as novel processes for their preparation. In preferred embodiments, bile acids are provided herein which have substituents on the B-ring and/or D-ring side chain and optionally on the hydroxy group of the A-ring.

Total Synthesis of Cortisol: Application to Selective Deuteriation at C-1 and C-19

An 11-step total synthesis of cortisol and its application to selective deuteriation at the 19-methyl and the C-1 positions is described.The dihydroxy acetone group at C-17 of prednisone (3) was protected as the bismethylenedioxy derivative (4) and degraded to the ring C/D fragment, oxoindanylpropionic acid (2), by Birch reduction followed by ozonolysis.The reaction of deuterioisopropenyl anion with compound (2) followed by dehydration, cyclisation, and osonolysis produced -4,5-seco-17α,20;20,21-bismethylenedioxypregnane-3,5,11-trione .Cyclisation of (16a) in KOH-MeOH affordedthe bismethylenedioxy cortisone (17), wich upon reduction with KBH4 gave the desired (2)H5 cortisol (19).