TY - JOUR
T1 - Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids
AU - Fleary-Roberts, Nadia
AU - Lemière, Gilles
AU - Clayden, Jonathan
PY - 2015/9/30
Y1 - 2015/9/30
N2 - Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.
AB - Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.
KW - Alkene
KW - Coupling
KW - Metalcatalysed
KW - Natural product synthesis
UR - http://www.scopus.com/inward/record.url?scp=84939255057&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2015.02.055
DO - 10.1016/j.tet.2015.02.055
M3 - Article (Academic Journal)
AN - SCOPUS:84939255057
SN - 0040-4020
VL - 71
SP - 7204
EP - 7208
JO - Tetrahedron
JF - Tetrahedron
IS - 39
ER -