A Kiyooka aldol approach for the synthesis of the C(14)-C(23) segment of the diastereomeric analog of tedanolide C.
The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.
Centre for Biomolecular Drug Research, Leibniz Universität Hannover, 30167 Hannover, Germany.
Leila
L
Bülow
Arun
A
Naini
Jörg
J
Fohrer
Markus
M
Kalesse
D000447:Aldehydes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D018942:Macrolides; C516408:tedanolide C; D002244:Carbon; C116609:3-hydroxybutanal