54397-80-7Relevant academic research and scientific papers
Stereospecific solid state sodium borohydride reductions of cage diketones
Marchand,Madhusudhan Reddy
, p. 6571 - 6576 (1991)
Solid state reductions of carbonyl groups in three cage diketones, 1a-1c, have been performed by using sodium borohydride, and the results thereby obtained have been compared with the corresponding reductions performed in ethanol solution. In each case, the solid state reduction proceeds stereospecifically; hydride transfer occurs exclusively at the exo face of the carbonyl group. In contrast, the corresponding homogeneous (solution-phase) reductions display only moderate stereoselectivity.
D3-trishomocubane-4-carboxylic acid as a new chiral building block: Synthesis and absolute configuration
Gaidai, Alexandr V.,Volochnyuk, Dmitriy M.,Shishkin, Oleg V.,Fokin, Andrey A.,Levandovskiy, Igor A.,Shubina, Tatyana E.
, p. 810 - 816 (2012/05/07)
The preparation of (±)-D3-trishomocubanone on a multigram scale from 1,4-benzoquinone and cyclopentadiene was optimized to give the target product in 39% overall yield, that was transformed to (±)-D 3-trishomocubane-4-carboxylic acid via a three-step procedure involving the Corey-Chaykovsky reaction followed by boron trifluoride-diethyl ether catalyzed epoxide ring opening and further oxidation. Optically active (+)-D3-trishomocubane-4-carboxylic acid was prepared through the resolution of the racemate by crystallization of its salt with (R)-phenylethylamine; the absolute configuration was assigned by X-ray crystal structure analysis. Georg Thieme Verlag Stuttgart · New York.
A NOVEL, VERSATILE SYNTHETIC APPROACH TO LINEARLY FUSED TRICYCLOPENTANOIDS via PHOTO-THERMAL OLEFIN METATHESIS
Mehta, Goverdhan,Srikrishna, A.,Reddy, A. Veera,Nair, Mangalam S.
, p. 4543 - 4559 (2007/10/02)
Fifteen examples of a new, speedy and general approach to linearly fused tricyclopentanoids bearing the tricyclo2,6>undecane (triquinane) frame of high contemporary interest is delineated.The key concept in our synthetic sequence to tri
The reaction of potassium iodide in polyhydrogen fluoride-pyridine with two cage diols. A simple synthesis of tetracyclo4,11.05,9>undeca-2,6-diene ('homohypostrophene')
Dong, Dao Cong,Edward, John T.
, p. 1324 - 1326 (2007/10/02)
The diol 2 was converted by treatment with potassium iodide in polyhydrogen fluoride-pyridine into a mixture of the diiodide 5 and homohypostrophene 6.The diol 10 under the same conditions gave the ether 14.Treatment of the mixture of 5 and 6 with sodium in boiling tetrahydrofuran gave an easily-separable mixture of 6 and 7.
