Concerning the synthesis of the tedanolide C(13)-C(23) fragment via anti-aldol reaction.
Synthesis of C(13)-C(23) aldehyde 4, an important intermediate in a planned total synthesis of tedanolide, is described. The stereoselectivity of the key anti-aldol reaction of aldehyde 5 and ketone 6 (en route to 4) perfectly tracks the enantiomeric purity of 5. It is demonstrated that aldehyde 24, a precursor of 5, undergoes facile epimerization during a Swern oxidation and stabilized ylide olefination sequence.
Dunetz
Joshua R
JR
Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D007783:Lactones; D018942:Macrolides; C119775:tedanolide