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Synthesis of the Conjugated Tetraene Acid Side Chain of Mycolactone E by Suzuki–Miyaura Cross‐Coupling Reaction of Alkenyl Boronates
Author(s) -
Wang Yuan,
Dai WeiMin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301484
Subject(s) - chemistry , conjugated system , alkyne , polyene , catalysis , stereoselectivity , tetrahydrofuran , yield (engineering) , bromide , side chain , electrophile , tetrahydropyran , coupling reaction , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , ring (chemistry) , polymer , materials science , solvent , metallurgy
The conjugated tetraene acid side chain of mycolactone E has been synthesized by the cross‐coupling reaction of a trisubstituted triene bromide with a trisubstituted alkenyl boronate catalyzed by Pd(OAc) 2 –Aphos‐Y under mildly basic conditions [K 3 PO 4 · 3H 2 O, H 2 O, tetrahydrofuran (THF), 35 °C, 18 h]. The conjugated tetraene product was obtained in 85 % yield without geometrical isomer(s) under the catalytic conditions. These results demonstrated that the coupling of alkenyl halides with alkenyl boronates catalyzed by Pd(OAc) 2 –Aphos‐Y in combination with Cu I ‐catalyzed regio‐ and stereoselective alkyne borylation offers an efficient synthetic tool for accessing conjugated polyene molecules.