Stereoselective Addition of Pyridyl Lithium to 22‐Aldehyde Steroid. Synthesis of 22‐Piperidin‐yl‐pregnan‐3β, 22(S)‐diol

References

• Urbina , J. U. , Vivas , J. , Visbal , G. and Contreras , L. M. 1995 . Modification of sterol composition of Trypanosoma (Schizotrypanum) cruzi epimastigotes by Δ24(25)‐sterol methyl transferase inhibitors and their combinations with ketoconazole . Mol. Biochem. Parasi. , 73 : 199 – 210 . [CSA]
   Google Scholar
• Nes , W. D. , Janssen , G. G. , Norton , R. A. , Kalinowska , F. , Crumley , F. G. , Tal , B. , Bergenstrahles , A. and Jonsson , L. 1991 . Regulation of sterol biosynthesis in sunflower by 24(R,S),25‐epiminolanosterol, a novel C‐24 methyl transferase inhibitor . Biochem. Biophy. Res. Commun. , 177 ( 1 ) : 566 – 574 . [CSA] [CROSSREF]
   Google Scholar
• Nes , W. D. , Janssen , G. G. and Bergenstrahles , A. 1991 . Structural requirements for transformation of subtrates by the (S)‐Adenosyl‐L‐methionine:Δ24(25)‐sterol methyl transferase . J. Biol. Chem. , 266 ( 23 ) : 15202 – 15212 . [PUBMED] [INFOTRIEVE]
   Google Scholar
• Nes , W. D. , Guo , D. and Wen , Zhou . 1997 . Substrate‐based inhibitors of the (S)‐Adenosyl‐L‐methionine:Δ24(25)‐ to Δ24(28)‐sterol methyl transferase from Saccharomyces cerevisiae . Arch. Biochem. Biophys. , 342 ( 1 ) : 68 – 81 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   Google Scholar
• Ohtani , I. , Kusumi , T. , Kashman , Y. and Kakisawa , H. 1991 . High‐field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids . J. Am. Chem. Soc. , 113 : 4092 – 4096 .
   Web of Science ®Google Scholar
• Chérest , M. , Felkin , H. and Prudent , N. 1968 . Torsional strain involving partial bonds. The stereochemistry of the lithium aluminiun hydride reduction of some simple open‐chain ketones . Tetrahedron Lett. , 18 : 2199 – 2204 .
   Google Scholar
• Anh , N. T. and Eisenstein , O. 1977 . Theoretical interpretation of 1‐2 asymmetric induction. The importance of antiperiplanarity . Nouv. J. de Chim. , 1 ( 1 ) : 61 – 70 .
   Google Scholar
• Bartlett , P. A. 1980 . Stereocontrol in the synthesis of acyclic systems: applications to natural product synthesis . Tetrahedron , 36 : 3 – 72 . [CROSSREF]
   Google Scholar
• Piatak , D. M. and Wicha . 1978 . Various approaches to the construction of aliphatic side chains of steroids and related compounds . J. Chem. Rev. , 78 ( 3 ) : 199 – 241 .
   Google Scholar
• Barton , D. H.R. , Poyser , J. P. and Sammes , P. G. 1972 . Some stereoselective and regioselective olefin additions: iodoacetoxylation and realted electrophilic additions across the 22(23)‐bond of 3α,5α‐cycloergosta‐7,22‐dien‐6‐one . J. Chem. Soc., Perkin Trans. , 1 : 61
   Google Scholar
• Poyser , J. P. and Ourisson , G. 1974 . Stereospecific synthesis of (22R)‐22‐hydroxycholesterol and (22R)‐cholesta‐5,24‐diene‐3β,22‐diol . J. Chem. Soc., Perkin Trans. , 1 : 2061 – 2066 . [CROSSREF]
   Google Scholar
• Poyser , J. P. , Reinach‐Hirtzbach , F. and Ourisson , G. 1974 . The stereospecific synthesis of inotodiol 3β,22R‐dihydroxylanosta‐8,24‐diene . Tetrahedron , 30 : 977 – 986 . [CROSSREF]
   Google Scholar
• Eyley , E. C. and Williams , D. H. 1976 . Synthesis of 25‐hydroxyprovitamin D3 and 25ξ,26‐dihydroxyprovitamin D3 . J. Chem. Soc., Perkin Trans. , 1 : 731 – 735 . [CROSSREF]
   Google Scholar
• Hikino , H. , Okuyama , T. , Arihara , S. , Hikino , Y. , Takemoto , T. , Mori , H. and Shibata , K. 1975 . Shidasterone, an insect metamorphosing substance from Blechnum niponicum . Chem. Pharm. Bull. , 23 ( 7 ) : 1458 – 1479 . [PUBMED] [INFOTRIEVE]
   Google Scholar
• David Nes , W. 2000 . Sterol methyl transferase: enzymology and inhibition . Biochim. Biophys. Acta , 1529 : 63 – 88 .
   Google Scholar
• Atencio , Reinaldo , Visbal , Gonzalo , Pekera , Sara , Papale , Jham and Urbina , Julio A. 2001 . Studies of molecular structure parameters of 20‐piperidin‐2‐yl‐5α‐pregnan‐3β,20‐diol and its N‐methyl derivative: two inhibitors of Δ24(25)‐sterol methyl transferase and Δ24(24′)‐sterol methyl reductase of Trypanosoma cruzi . Acta Crystallogr. B, Structural Science , 57 : 714 – 721 . [CSA] [CROSSREF]
   Google Scholar