1611465-71-4Relevant academic research and scientific papers
Total Synthesis of (-)-Luminacin D
Malassis, Julien,Bartlett, Nathan,Hands, Kane,Selby, Matthew D.,Linclau, Bruno
, p. 3818 - 3837 (2016)
A second-generation synthesis of (-)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as the key improvement.
Stereocontrol by quaternary centres: A stereoselective synthesis of (-)-luminacin D
Bartlett, Nathan,Gross, Leona,Peron, Florent,Asby, Daniel J.,Selby, Matthew D.,Tavassoli, Ali,Linclau, Bruno
supporting information, p. 3306 - 3310 (2014/04/03)
Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.
