Concerning the synthesis of the tedanolide C(13)-C(23) fragment via anti-aldol reaction

Article abstract of DOI:10.1021/ol800546g

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.