Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa; Tomohiro Nagasawa; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2011.11.145

Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa, Tomohiro Nagasawa, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

9 Citations (Scopus)

Abstract

The first enantioselective synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane derivative incorporating a γ-lactone ring as its structural feature, has been achieved by using base-induced intramolecular cyclization of an epoxy nitrile intermediate to install its cyclobutane skeleton as well as three contiguous stereocenters as the key transformation.

Original language	English
Pages (from-to)	705-706
Number of pages	2
Journal	Tetrahedron Letters
Volume	53
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.145
Publication status	Published - 2012 Feb 8

Keywords

Caryophyllane
Cytotoxic
Epoxy nitrile cyclization
Rumphellaone A

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The first enantioselective synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane derivative incorporating a γ-lactone ring as its structural feature, has been achieved by using base-induced intramolecular cyclization of an epoxy nitrile intermediate to install its cyclobutane skeleton as well as three contiguous stereocenters as the key transformation.",

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AU - Nagasawa, Tomohiro

AU - Kuwahara, Shigefumi

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AB - The first enantioselective synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane derivative incorporating a γ-lactone ring as its structural feature, has been achieved by using base-induced intramolecular cyclization of an epoxy nitrile intermediate to install its cyclobutane skeleton as well as three contiguous stereocenters as the key transformation.

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