1421640-71-2Relevant academic research and scientific papers
Synthesis of 9-alkylated calcitriol and two 1α,25-dihydroxy-9- methylene-10,19-dihydrovitamin D3 analogues with a non-natural triene system by thermal sigmatropic rearrangements
Kulesza, Urszula,Sigüeiro, Rita,Mouri?o, Antonio,Sicinski, Rafal R.
, p. 1444 - 1450 (2013)
1α,25-(OH)2-9α-Methylvitamin D3 (4), the first known analogue of the natural hormone 1α,25-(OH)2D 3 (3) with an alkyl substituent at C-9, and two 1α,25-(OH) 2-9-methylene-10,19-dihydrovitamin D3 analogues (7 and 8) with an unprecedented non-natural triene system were synthesized by thermal isomerization of 1α,25-(OH)2-9-methylprevitamin D3 (6). Three alternative approaches (Sonogashira, Stille, or stereoselective dehydration of a tertiary propargyl alcohol) have been successfully used to construct the dienyne precursors of previtamin 6 possessing two methyl groups capable of participating in the [1,7]-sigmatropic hydrogen shift.
