Application of hitherto unexplored macrocyclization strategies in the epothilone series: novel epothilone analogs by total synthesis.
A total synthesis of Epothilone 490 and a synthesis of 11-hydroxy dEpoB utilizing a vinyl-boronate cross-metathesis followed by a Suzuki macrocyclization. A mild route to reach aldehydes from terminal olefins, anticipating Nozaki-Kishi macrocyclization is described.
Njardarson
Jon T
JT
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, New York, NY 10021, USA.
Biswas
Kaustav
K
Danishefsky
Samuel J
SJ
D003500:Cyclization; D034261:Epothilones / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis; D013844:Thiazoles / Q000138:chemical synthesis
D034261:Epothilones; D007202:Indicators and Reagents; D018942:Macrolides; D013844:Thiazoles; C466502:epothilone 490