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 journalArticle

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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

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Acetogenins
Lactones
Sulfones
Stereoisomerism
Epoxy Compounds
Alkylation
Biological Products
bullatacin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bisepi-Bullatacin. / Naito, Hiroyuki; Kawahara, Eiji; Maruta, Katsunori; Maeda, Minoru; Sasaki, Shigeki.

In: Journal of Organic Chemistry, Vol. 60, No. 14, 01.07.1995, p. 4419-4427.

Research output: Contribution to journalArticle

Naito, Hiroyuki ; Kawahara, Eiji ; Maruta, Katsunori ; Maeda, Minoru ; Sasaki, Shigeki. / The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bisepi-Bullatacin. In: Journal of Organic Chemistry. 1995 ; Vol. 60, No. 14. pp. 4419-4427.
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