Total synthesis of merrilactone A

Masayuki Inoue; Takaaki Sato; Masahiro Hirama

doi:10.1021/ja036587+

Total synthesis of merrilactone A

Masayuki Inoue, Takaaki Sato, Masahiro Hirama

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

110 Citations (Scopus)

Abstract

Merrilactone A (1) has been shown to possess neurotrophic activity and thus is expected to hold therapeutic potential in the treatment of neurodegeneration diseases. In this paper, we report the total synthesis of (±)-1, employing, as key steps, a novel desymmetrization protocol of meso-diketone to construct the core cis-bicyclo[3.3.0]octyl system of 1 (3 → 2) and a radical cyclization to install the highly congested C9-quaternary carbon (16 → 17).

Original language	English
Pages (from-to)	10772-10773
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	36
DOIs	https://doi.org/10.1021/ja036587+
Publication status	Published - 2003 Sept 10
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Sato, Takaaki

AU - Hirama, Masahiro

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AB - Merrilactone A (1) has been shown to possess neurotrophic activity and thus is expected to hold therapeutic potential in the treatment of neurodegeneration diseases. In this paper, we report the total synthesis of (±)-1, employing, as key steps, a novel desymmetrization protocol of meso-diketone to construct the core cis-bicyclo[3.3.0]octyl system of 1 (3 → 2) and a radical cyclization to install the highly congested C9-quaternary carbon (16 → 17).

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Total synthesis of merrilactone A

Abstract

ASJC Scopus subject areas

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