Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin

Takahiro Suzuki; Yuria Miyajima; Kaname Suzuki; Kanako Iwakiri; Masaki Koshimizu; Go Hirai; Mikiko Sodeoka; Susumu Kobayashi

doi:10.1021/ol400549q

Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin

Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi

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

26 Citations (Scopus)

Abstract

The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

Original language	English
Pages (from-to)	1748-1751
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/ol400549q
Publication status	Published - Apr 5 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol400549q

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title = "Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin",

abstract = "The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.",

author = "Takahiro Suzuki and Yuria Miyajima and Kaname Suzuki and Kanako Iwakiri and Masaki Koshimizu and Go Hirai and Mikiko Sodeoka and Susumu Kobayashi",

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T1 - Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin

AU - Suzuki, Takahiro

AU - Miyajima, Yuria

AU - Suzuki, Kaname

AU - Iwakiri, Kanako

AU - Koshimizu, Masaki

AU - Hirai, Go

AU - Sodeoka, Mikiko

AU - Kobayashi, Susumu

PY - 2013/4/5

Y1 - 2013/4/5

N2 - The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

AB - The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

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JO - Organic Letters

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ER -

Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin

Abstract

All Science Journal Classification (ASJC) codes

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