Ruthenium-catalyzed cycloisomerization and its application to the synthesis of (±)-cinchonaminone

Takao Ogawa; Tomonori Nakamura; Takuya Araki; Koujirou Yamamoto; Satoshi Shuto; Mitsuhiro Arisawa

doi:10.1002/ejoc.201200260

Ruthenium-catalyzed cycloisomerization and its application to the synthesis of (±)-cinchonaminone

Takao Ogawa, Tomonori Nakamura, Takuya Araki, Koujirou Yamamoto, Satoshi Shuto, Mitsuhiro Arisawa

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

9 Citations (Scopus)

Abstract

Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (±)-cinchonaminone.

Original language	English
Pages (from-to)	3084-3087
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201200260
Publication status	Published - 2012 Jun
Externally published	Yes

Keywords

Cyclization
Heterocycles
Natural products
Ruthenium
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (±)-cinchonaminone.",

keywords = "Cyclization, Heterocycles, Natural products, Ruthenium, Total synthesis",

author = "Takao Ogawa and Tomonori Nakamura and Takuya Araki and Koujirou Yamamoto and Satoshi Shuto and Mitsuhiro Arisawa",

year = "2012",

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doi = "10.1002/ejoc.201200260",

language = "English",

pages = "3084--3087",

journal = "Annalen der Pharmacie",

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T1 - Ruthenium-catalyzed cycloisomerization and its application to the synthesis of (±)-cinchonaminone

AU - Ogawa, Takao

AU - Nakamura, Tomonori

AU - Araki, Takuya

AU - Yamamoto, Koujirou

AU - Shuto, Satoshi

AU - Arisawa, Mitsuhiro

PY - 2012/6

Y1 - 2012/6

N2 - Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (±)-cinchonaminone.

AB - Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (±)-cinchonaminone.

KW - Cyclization

KW - Heterocycles

KW - Natural products

KW - Ruthenium

KW - Total synthesis

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JF - Annalen der Pharmacie

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