The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bisepi-Bullatacin

Article abstract of DOI:10.1021/jo00119a019

This paper reports the first total synthesis of the natural product (+)-bullatacin (1), a representative of potent antitumor Annonaceous acetogenins, as well as a stereoisomer (+)-(15,24)-bisepi-bullatacin (2).In this synthesis, a new, efficient method has been developed to introduce the γ-lactone into the bistetrahydrofuran skeleton through in situ alkylation of epoxide 4 by the α-sulfonyl carbanion of phenylsulfone 5.The methylated γ-lactone was successfully synthesized by a sequence of reactions comprising an aldol reaction, an acidic lactonization, and elimination under mild, basic condition.