6507-91-1Relevant academic research and scientific papers
One-flask tethered ring closing metathesis-electrocyclic ring opening for the highly stereoselective synthesis of conjugated Z/E-dienes
Schmidt, Bernd,Kunz, Oliver
, p. 1008 - 1018 (2012/03/27)
A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised. Ring closing metathesis (RCM) of butenoates derived from allylic alcohols can be combined with base-induced ring opening in a one-flask sequence. In this way, dienoic acids become accessible in an operationally simple procedure in very high yields and excellent stereoselectivities, with the tether remaining in the product as a valuable functional group for further transformations. Copyright
A STEREOSELECTIVE SYNTHESIS OF (2Z,4E)-DIENOIC ACID INVOLVING MASKED FUNCTIONAL GROUPS: n-Bu4NF INDUCED RING-OPENING OF α,β-UNSATURATED δ-LACTONE
Nakata, Tadashi,Hata, Noriaki,Oishi, Takeshi
, p. 333 - 334 (2007/10/02)
n-Bu4NF induced ring-opening of α,β-unsaturated δ-lactone produced (2Z,4E)-dienoic acid without affecting acetoxyl groups present in the side chain of the lactone ring.
