191480-99-6Relevant academic research and scientific papers
Total synthesis of (±)-furoscrobiculin B
Seki, Maki,Sakamoto, Toshihiro,Suemune, Hiroshi,Kanematsu, Ken
, p. 1707 - 1714 (1997)
Total synthesis of (±)-furoscrobiculin B, a lactarane sesquiterpene isolated from basidiomycetes of mushrooms, has been achieved via an improved synthetic route of our previous work based on a Furan Ring Transfer (FRT) reaction and base-catalysed pinacol-type rearrangement.
Furan approach to vitamin D analogues. Synthesis of the A-ring of calcitriol and 1α-hydroxy-3-deoxyvitamin D3
Miles, William H.,Connell, Katelyn B.,Ulas, Goezde,Tuson, Hannah H.,Dethoff, Elizabeth A.,Mehta, Varun,Thrall, April J.
supporting information; experimental part, p. 6820 - 6829 (2010/12/18)
The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel-Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield.
Furan approach to the synthesis of the A-ring of Vitamin D analogues
Miles, William H.,Connell, Katelyn B.
, p. 1161 - 1163 (2007/10/03)
The efficient transformation of 2,3-disubstituted furan (3) into (Z)-dienol (2) illustrates a useful strategy for the synthesis of the A-ring of Vitamin D analogues.
