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

Hiroyuki Naito, Eiji Kawahara, Katsunori Maruta, Minoru Maeda, Shigeki Sasaki

Research output: Contribution to journalArticlepeer-review

92 Citations (Scopus)

Abstract

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 phenyl sulfone 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.

Original languageEnglish
Pages (from-to)4419-4427
Number of pages9
JournalJournal of Organic Chemistry
Volume60
Issue number14
DOIs
Publication statusPublished - Jul 1 1995

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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