Total Synthesis of (+)-Muconin

Takehiko Yoshimitsu, Toshiyuki Makino, Hiroto Nagaoka

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

(+)-Muconin (1), isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is a sequential THF/THP-possessing acetogenin that exhibits potent and selective in vitro cytotoxicity toward pancreatic and breast tumor cell lines. In this study, a new route was established for obtaining (+) -muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel α-C-H hydroxyalkylation and α′-C-H oxidation of tetrahydrofuran.

Original languageEnglish
Pages (from-to)1993-1998
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number6
DOIs
Publication statusPublished - Mar 19 2004
Externally publishedYes

Fingerprint

Acetogenins
Cytotoxicity
Tumors
Cells
Oxidation
muconin
Mucous Membrane
muricatacin
tetrahydrofuran

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total Synthesis of (+)-Muconin. / Yoshimitsu, Takehiko; Makino, Toshiyuki; Nagaoka, Hiroto.

In: Journal of Organic Chemistry, Vol. 69, No. 6, 19.03.2004, p. 1993-1998.

Research output: Contribution to journalArticle

Yoshimitsu, Takehiko ; Makino, Toshiyuki ; Nagaoka, Hiroto. / Total Synthesis of (+)-Muconin. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 6. pp. 1993-1998.
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