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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10.1016/j.tetlet.2011.11.145

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title = "Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization",

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.",

keywords = "Caryophyllane, Cytotoxic, Epoxy nitrile cyclization, Rumphellaone A",

author = "Takafumi Hirokawa and Tomohiro Nagasawa and Shigefumi Kuwahara",

note = "Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 22380064 ). ",

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T1 - Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization

AU - Hirokawa, Takafumi

AU - Nagasawa, Tomohiro

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 22380064 ).

PY - 2012/2/8

Y1 - 2012/2/8

N2 - 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.

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.

KW - Caryophyllane

KW - Cytotoxic

KW - Epoxy nitrile cyclization

KW - Rumphellaone A

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M3 - Article

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EP - 706

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 6

ER -

Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization

Abstract

Keywords

ASJC Scopus subject areas

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