218434-90-3Relevant articles and documents
Synthesis of Optically Active Maresin 2 and Maresin 2 n-3 DPA
Ogawa, Narihito,Amano, Takahito,Kobayashi, Yuichi
supporting information, p. 295 - 298 (2020/11/18)
Maresins are among the most potent antiinflammatory lipid metabolites. We report stereoselective syntheses of maresin 2 and maresin 2 n-3 DPA. The anti -diol was constructed through epoxide ring opening of an optically active β,γ-epoxy aldehyde, synthesized in situ by Swern oxidation of the corresponding alcohol. Finally, the target compounds were synthesized through a Sonogashira coupling of a C9-C22 iodide and methyl (Z)-oct-4-en-7-ynoate or methyl oct-7-ynoate, respectively.
Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965
Kobayashi, Yuichi,Yamaguchi, Kai,Morita, Masao
, p. 1826 - 1831 (2018/03/07)
Allylic substitution of secondary γ,γ-disubstituted allylic picolinates with ArMgBr-based copper reagents was applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity (99%). Ozonolysis, addition of c-Hex-MgBr to the resulting aldehyde, and reductive amination with the piperazine derivative afforded LY426965.
Stereodivergent Intramolecular C(sp3)-H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N -Heterotricycles
Lindsay, Vincent N. G.,Viart, Hélène M.-F.,Sarpong, Richmond
supporting information, p. 8368 - 8371 (2015/07/15)
A general approach for the formation of five-membered saturated heterocycles by intramolecular C(sp3)-H functionalization is reported. Using N-sulfonyltriazoles as Rh(II) azavinyl carbene equivalents, a wide variety of stereodefined cis-2,3-dis