34545-87-4Relevant academic research and scientific papers
1,3-Diaxially substituted trans-decalins: Potential nonsteroidal human progesterone receptor inhibitors
Li, Ze,Watkins, E. Blake,Liu, Hua,Chittiboyina, Amar G.,Carvalho, Paulo B.,Avery, Mitchell A.
, p. 7764 - 7767 (2008)
(Chemical Equation Presented) On the basis of molecular modeling and QSAR analysis of the known human progesterone receptor (hPR) inhibitor Mifepristone (RU-486) and other hPR ligands, a new class of potential nonsteroidal hPR inhibitors was designed. The parent racemic compound 1 was synthesized through an efficient 13-step synthetic pathway. The key constructive steps are a stereoselective epoxide ring opening and the reductive Heck cyclization to form the main framework of (±)-1. The current established flexible synthetic route allows for further chemical diversification.
High-pressure Diels-Alder reactions of bicyclic dienones. Short syntheses of hydrophenanthrenones
Minuti, Lucio,Taticchi, Aldo,Gacs-Baitz, Eszter,Wenkert, Ernest
, p. 10033 - 10040 (1995)
Diels-Alder reactions of a heteroannular bicyclic dienone with acyclic dienes under Lewis acid catalysis at atmospheric and 7 Kbar pressure and presented. The pressure reactions are fast, high-yielding and highly diastereoselective en route to hydrophenanthrenones. As a consequence of some post-cycloaddition enolization, both cis and trans products are available.
Three bacteriorhodopsins with ring-didemethylated 6-s-locked chromophores and their properties
Groesbeek, M.,Galen, A. J. J. van,Ippel, J. H.,Berden, J. A.,Lugtenburg, J.
, p. 237 - 246 (2007/10/02)
Three novel, 6-s-locked rigidified retinals, racemic all-E 1,5-didemethyl-8,16-methanoretinal, all-E, 1,1-didemethyl-8,18-methanoretinal and all-E 8a,18-didehydro-1,1-didemethyl-8,18-methanoretinal were prepared in good yield in high purity on a 100-mg scale.For the preparation of the key intermediate in the synthesis of 1,5-didemethyl-8,16-methanoretinal, reductive cyanation of an unsaturated cyanohydrin to the corresponding conjugated nitrile was accomplished using triethylsilane and trifluoroacetic acid.The three locked retinals interact with bacterioopsin to form bacteriorhodopsin with about the same rate as the native chromophore.This work proves that steric interaction of the 1,1-dimethyl group in the chromophore is an important factor in binding to bacterioopsin.
