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

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

12 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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10.1016/j.tet.2012.04.035

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title = "Synthesis of rumphellaone A via epoxy nitrile cyclization",

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.",

keywords = "Cyclobutane, Cytotoxic, Epoxy nitrile, Rumphellaone, Total synthesis",

author = "Takafumi Hirokawa and Shigefumi Kuwahara",

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

year = "2012",

month = jun,

day = "17",

doi = "10.1016/j.tet.2012.04.035",

language = "English",

volume = "68",

pages = "4581--4587",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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T1 - Synthesis of rumphellaone A via epoxy nitrile cyclization

AU - Hirokawa, Takafumi

AU - Kuwahara, Shigefumi

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

PY - 2012/6/17

Y1 - 2012/6/17

N2 - 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.

AB - 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.

KW - Cyclobutane

KW - Cytotoxic

KW - Epoxy nitrile

KW - Rumphellaone

KW - Total synthesis

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DO - 10.1016/j.tet.2012.04.035

M3 - Article

AN - SCOPUS:84861220927

VL - 68

SP - 4581

EP - 4587

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 24

ER -

Synthesis of rumphellaone A via epoxy nitrile cyclization

Abstract

Keywords

ASJC Scopus subject areas

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