Large-Scale Synthesis Of Eldecalcitol

Hyung Wook Moon,Seung Jong Lee, Seong Hu Park, Se Gyo Jung, In A Jung, Chang Hun Seol,Seung Woo Kim, Seon Mi Lee,Bogonda Gangganna,Seokhwi Park,Kee-Young Lee,Chang-Young Oh,Juyoung Song,Jaehun Jung, Ji Soo Heo,Kang Hee Lee, Hae Sol Kim, Won Taek Lee,Areum Baek,Hyunik Shin

ORGANIC PROCESS RESEARCH & DEVELOPMENT(2021)

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Abstract
Industrial-scale synthesis of eldecalcitol is described. AA highly diastereoselective epoxidation of p-methoxybenzyl (PMB) protected dienol at room temperature provides the key epoxide intermediate with a secondary hydroxyl group, which is alkylated with a triflate to set up all of the subunits at the C-1, C-2, and C-3 positions of the A-ring fragment. Selective protecting group manipulation followed by palladium-catalyzed cyclization then provides the A-ring synthon. The C/D-ring fragment is obtained by (1) direct C-H hydroxylation of Grundman's ketone using in situ prepared trifluoropropanone dioxirane and (2) protection. Finally, the coupling of the A-ring with the C/D-ring fragment, global deprotection, and recrystallization provide the highly crystalline eldecalcitol.
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Key words
eldecalcitol, C-2-symmetric, C-H hydroxylation, Sharpless epoxidation, triflate alkylation
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