67392-10-3Relevant academic research and scientific papers
A new chiral synthesis of bullfrog bile sterol 5β-ranol
Harney, Don W.,Macrides, Theodore A.
, p. 1353 - 1356 (2007/10/03)
(24R)-27-Nor-5β-cholestane-3α,7α,12α,24,26-pentol (5β-ranol) has been synthesised by the Wittig olefinic coupling of a steroidal module and a side-chain module followed by reduction and deprotection. The steroidal module is derived from cholic acid by a one-carbon degradation of the side chain to produce norcholic acid followed by the loss of a second carbon in an iododecarboxylation and then synthesis of the triphenylphosphonium iodide. The side-chain module is derived from (S)-(-)-butane-1,2,4-triol by benzylidene protection of the 2,4-diol followed by Swern oxidation to the aldehyde. This general synthetic scheme could be used to produce a range of bile sterols with the (24R)-hydroxy moiety which may have significant hepatoprotective activity against liver damage induced by free radicals or reactive metabolites.
Synthesis of (24R)- and (24S)-27-Nor-5β-cholestane-3α,7α,12α,24,26-pentols
Kuramoto, Taiju,Noma, Yukio,Hoshita, Takahiko
, p. 1330 - 1334 (2007/10/02)
(24R)- and (24S)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentols were synthesized, starting from 3α,7α,12α-trihydroxy-5β-cholan-24-al, by means of the Reformatsky reaction with bromoacetate and subsequent lithium aluminum hydride reduction of the resulting (24R)- and (24S)-3α,7α,12α,24-tetrahydroxy-27-nor-5β-cholestan-26-oates.The configurations at C-24 of the synthetic pentols were assigned by 13C-nuclear magnetic resonance spectroscopy.By direct comparison with a synthetic specimen, 5β-ranol, the major bile constituent of bullfrog, was shown to be (24R)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol.The availability of the 24S-epimer of 5β-ranol enabled us to ascertain the absence of this bile alcohol in the bullfrog bile. Keywords---synthesis; bile alcohol; bullfrog; structural determination; (24R)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol; (24S)-27-nor-5β-cholestane-3α,7α,12α,24,26-pentol; 13C-NMR; 5β-ranol
