37609-34-0Relevant academic research and scientific papers
Stereochemical control in the still-wittig rearrangement synthesis of cyclohexyl (Z)- alkene inhibitors of Pin1
Chen, Xingguo R.,Fan, Shuang A.,Ware, Rachel I.,Etzkorn, Felicia A.
, (2015)
Three stereoisomeric inhibitors of Pin1: (2R,5S)-, (2S,5R)- and (2S,5S)-Ac-pSer-ψ[(Z) CH = C]-pipecolyl(Pip)-2-(2-naphthyl)ethylamine 1, that mimic L-pSer-D-Pro, D-pSer-LPro, and D-pSer-D-Pro amides respectively, were synthesized by a 13-step route. The newly formed stereogenic centers in the pipecolyl ring were introduced by Luche reduction, followed by stereospecific [2,3]-Still-Wittig rearrangement. The (Z)- to (E)-alkene ratio in the rearrangements were consistently 5.5 to 1. The stereochemistry at the original Ser α-carbon controlled the stereochemistry of the Luche reduction, but it did not affect the stereochemical outcome of the rearrangement, which consistently gave the (Z)-alkene. The epimerized by-product, (2S,5S)-10, resulting from the work-up after Na/NH3 debenzylation of (2S,5R)- 9, was carried on to the (2S,5S)-1 isomer. Compound (2S,5S)-10 was resynthesized from the Luche reduction by-product, (2R,3R)-3, and the stereochemistry was confirmed by comparison of the optical rotations. The IC50 values for (2R,5S)-1, (2S,5R)-1 and (2S,5S)-1 Pin1 inhibition were: 52, 85, and 140 μM, respectively.
A Simple Method for Producing Cycloalkenyllithiums from Cycloalkanones via Reductive Lithiation of Enol Phenyl Thioethers
Cohen, Theodore,Doubleday, Mary Dosch
, p. 4784 - 4786 (2007/10/02)
Cyclohexenyl, cycloheptenyl, and cyclooctenyl phenyl sulfides, readily prepared from the corresponding cycloalkanones, are reductively lithiated by lithium p,p'-di-tert-butylbiphenylide to produce cycloalkenyllithiums in good yields.
STUDIES OF THE STABILITY AND RECTIVITY OF SUBSTITUTED VINYL TITANIUM TRIISOPROPOXIDES
Boeckman, Robert K. Jr.,O'Connor, Kenneth J.
, p. 3271 - 3274 (2007/10/02)
The stability and reactivity of vinyl titanium triisopropoxides having a variety of substitution patterns has been explored.These reagents when prepared in Et2O have proven to be more stable than expected based on prior reports, and they exhibit sufficien
Cycloalkenyl analogues of prostaglandins E
-
, (2008/06/13)
Analogues of prostaglandins A, E, and F in which the C13 -C20 chain of the natural prostaglandins is replaced by a cycloalkenyl or a hydroxycycloalkenyl moiety such that vinylene radical and the hydroxyl group of the ring respectivel
