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

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

Access to Document

10.1016/j.tetlet.2011.11.145

Cite this

@article{3c5088d26f87443ca0077ee4406ec45a,

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 ). ",

year = "2012",

month = feb,

day = "8",

doi = "10.1016/j.tetlet.2011.11.145",

language = "English",

volume = "53",

pages = "705--706",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "6",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84855435411&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84855435411&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.11.145

DO - 10.1016/j.tetlet.2011.11.145

M3 - Article

AN - SCOPUS:84855435411

VL - 53

SP - 705

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

Access to Document

Other files and links

Fingerprint

Cite this