Group 4 metals in polyketide synthesis: a convergent strategy for the synthesis of polypropionate-derived (E,E)-trisubstituted 1,3-dienes.
[reaction: see text] A convergent Group 4 metal-mediated coupling process is described for the synthesis of polypropionate-derived (E,E)-1,3-dienes. Both the stereochemistry of the internal alkyne and the presence/absence of a tethered alkoxide on this pi-component were found to play critical roles in dictating the regiochemical course of these reactions.
Shimp
Heidi L
HL
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Micalizio
Glenn C
GC
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D028561:Transition Elements / Q000737:chemistry*
D000475:Alkenes; D018942:Macrolides; D011422:Propionates; D028561:Transition Elements