152931-03-8Relevant articles and documents
Radical cyclization route to the stereoselective synthesis of ( )-trans-cognac lactone and ( )-trans-aerangis lactone
Sabitha, Gowravaram,Bhikshapathi,Yadav
, p. 561 - 569 (2007/10/03)
Stereoselective total synthesis of two chiral lactones, (+)-trans-cognac lactone (1b) and (+)-trans-aerangis lactone (2c), has been achieved from the same intermediate using a radical-based cyclization route. Copyright Taylor & Francis Group, LLC.
NEW METHODS FOR REDUCTIVE FREE-RADICAL CYCLIZATIONS OF α-BROMOACETALS TO 2-ALKOXYTETRAHYDROFURANS WITH ACTIVATED CHROMIUM(II)-ACETATE
Hackmann, Claus,Schaefer, Hans J.
, p. 4559 - 4574 (2007/10/02)
A method for the synthesis of γ-butyrolactones 6 is described in which the key step is a free-radical cyclization of α-bromoacetals 4 to 2-alkoxytetrahydrofurans 5 in 54-93percent yield induced by activated chromium(II)-acetate.Four new methods have been developed in order to activate the transition metal.Two of them require only catalytic amounts of chromium(II)-acetate, because it can be regenerated in situ chemically or electrochemically.The diastereoselectivity of the cyclization depends on the substitution pattern of 4 and ranges between 30.4:1 and 1:54.8.