Synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa; Shigefumi Kuwahara

doi:10.1016/j.tet.2012.04.035

Synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

10 Citations (Scopus)

Abstract

The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.

Original language	English
Pages (from-to)	4581-4587
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2012.04.035
Publication status	Published - 2012 Jun 17

Keywords

Cyclobutane
Cytotoxic
Epoxy nitrile
Rumphellaone
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.",

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author = "Takafumi Hirokawa and Shigefumi Kuwahara",

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language = "English",

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AU - Kuwahara, Shigefumi

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KW - Total synthesis

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