Synthesis of the C1-C13 tetraenoate subunit of the chivosazoles.
Using a combination of asymmetric vinylogous Mukaiyama aldol and Stille cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK. ip100@cam.ac.uk
Kan
S B Jennifer
SB
Gibson
Lisa J
LJ
D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D018942:Macrolides; D011090:Polyenes; D014753:Vinyl Compounds; C096623:chivosazol A; C003763:vinyl bromide