78969-35-4Relevant articles and documents
Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A
Anderson, Oren P.,Barrett, Anthony G.M.,Edmunds, Jeremy J.,Hachiya, Shun-Ichiro,Hendrix, James A.,Horita, Kiyoshi,Malecha, James W.,Parkinson, Christopher J.,Vansickle, Andrew
, p. 1562 - 1592 (2007/10/03)
The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.