329346-98-7Relevant academic research and scientific papers
Formal synthesis of (+/-)-guanacastepene A.
Shi,Hawryluk, Natalie A,Snider, Barry B
, p. 1030 - 1042 (2003)
A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 with
Synthesis of the hydroazulene ring system of guanacastepene.
Snider,Hawryluk
, p. 569 - 572 (2001)
[reaction: see text] A 12-step synthesis of 26, the functionalized hydroazulenone ring of guanacastepene (1), has been completed using the EtAlCl(2)-initiated cyclization of gamma,delta-unsaturated ketone 13 to construct 2,2,3-trisubstituted cyclopentanone 14, the palladium-catalyzed coupling of vinylmagnesium bromide with enol triflate 17 to prepare triene 21, and olefin metathesis of triene 21 to form the key hydroazulene 20.
