Synthesis of the C1-C12 fragment of iriomoteolide 1a by sequential catalytic asymmetric vinylogous aldol reactions.
An efficient synthesis of the C1-C12 fragment of iriomoteolide 1a has been accomplished via sequential application of two catalytic, asymmetric, vinylogous aldol reactions: a catalytic vinylogous aldol reaction was used to enantioselectively introduce the C5-C8 segment, and a second catalytic vinylogous aldol reaction was used to install the remaining two stereocenters and a stereodefined alkene in the form of an alpha,beta-unsaturated delta-lactone in one step.
Fang
Lijing
L
Department of Chemistry, Texas A&M University, College Station, Texas 77842-3092, USA.
Xue
Haoran
H
Yang
Jiong
J
D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D018942:Macrolides; D014753:Vinyl Compounds; C520799:iriomoteolide-1a; D002244:Carbon; C116609:3-hydroxybutanal