Total Synthesis of (+)-Muconin

Takehiko Yoshimitsu; Toshiyuki Makino; Hiroto Nagaoka

doi:10.1021/jo0303721

Total Synthesis of (+)-Muconin

Takehiko Yoshimitsu, Toshiyuki Makino, Hiroto Nagaoka

Research output: Contribution to journal › Article › peer-review

55 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 language	English
Pages (from-to)	1993-1998
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	69
Issue number	6
DOIs	https://doi.org/10.1021/jo0303721
Publication status	Published - Mar 19 2004
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo0303721

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title = "Total Synthesis of (+)-Muconin",

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.",

author = "Takehiko Yoshimitsu and Toshiyuki Makino and Hiroto Nagaoka",

year = "2004",

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doi = "10.1021/jo0303721",

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T1 - Total Synthesis of (+)-Muconin

AU - Yoshimitsu, Takehiko

AU - Makino, Toshiyuki

AU - Nagaoka, Hiroto

PY - 2004/3/19

Y1 - 2004/3/19

N2 - (+)-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.

AB - (+)-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.

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U2 - 10.1021/jo0303721

DO - 10.1021/jo0303721

M3 - Article

C2 - 15058945

AN - SCOPUS:1642355334

SN - 0022-3263

VL - 69

SP - 1993

EP - 1998

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Total Synthesis of (+)-Muconin

Abstract

ASJC Scopus subject areas

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