The preparation of α,ω-diynes with methyl groups at the termini (11a-i) is described. The methylene groups between the alkyne units vary between n = 12 (a) and n = 4 (i). Ring closing metathesis with Mo(CO) 6/CF3C6H4OH yielded the monocyclic alkyne 12a with 11a as starting material, whereas 11b-g yielded the cyclic diynes 13b-g. Detailed structural parameters were obtained for 13b and 13c by X-ray crystallography.
Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir
A practical and asymmetric synthesis of a functionalized trans-cyclopropoxy building block for the preparation of the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular SN2 displacement-ring closure, followed by a Baeyer-Villiger oxidation, yields the desired trans-cyclopropanol with full control of diastereoselectivity. A terminal alkyne is then effectively installed using LiNH(CH2)2NEt2. Starting from (S)-epichlorohydrin, the cyclopropoxy building block is prepared in 51% overall yield with >99.8% optical purity without isolation of any intermediates.
Xu, Feng,Zhong, Yong-Li,Li, Hongming,Qi, Ji,Desmond, Richard,Song, Zhiguo J.,Park, Jeonghan,Wang, Tao,Truppo, Matthew,Humphrey, Guy R.,Ruck, Rebecca T.
supporting information
p. 5880 - 5883
(2017/11/10)
Intramolecular cyclohexadienone annulations of fischer carbene complexes: Model studies for the synthesis of phomactins
The intramolecular cyclohexadienone annulation of chromium carbene complexes is examined as a method to provide general access to the Phomactin family of natural products. The importance of the stereochemistry of the carbene complex and the number of carbons in the tether connecting the carbene complex and the alkyne are probed. Additionally, the degree of the 1,4-asymmetric induction is examined.
Huang, Jie,Wang, Huan,Wu, Chunrui,Wulff, William D.
p. 2799 - 2802
(2008/02/05)
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