202062-48-4Relevant academic research and scientific papers
'Abnormal' eight-membered ring formation through S(N)2' intramolecular Nozaki/Kishi reaction in a synthetic approach to a taxane precursor
Muller, Benoit,Ferezou, Jean-Pierre,Lallemand, Jean-Yves,Pancrazi, Ange,Prunet, Joelle,Prange, Thierry
, p. 279 - 282 (1998)
Two different reactions were experimented for the construction of the eight-membered B-ring of taxane skeleton through the formation of the C9-C10 bond. A SmI2 promoted radical reaction on seco-alkynyl aldehydes 11cis or 11trans failed. A Nozaki/Kishi reaction carried out on the seco-iodovinyl aldehyde 12trans led, through an unprecedented intramolecular S(N)2' reaction, to the 'abnormally' cyclised product 14, the structure of which has been confirmed by X-ray crystalllography.
