Acid-Catalyzed Rearrangement of an Allene-Cyclohexenone Photoadduct and its Application in the Synthesis of (±)-Pentalenene

Tsumoru Morimoto; Tomoyuki Horiguchi; Kuriko Yamada; Ken Tsutsumi; Hideo Kurosawa; Kiyomi Kakiuchi

doi:10.1055/s-2004-815988

SPECIALTOPIC

Acid-Catalyzed Rearrangement of an Allene-Cyclohexenone Photoadduct and its Application in the Synthesis of (±)-Pentalenene

Tsumoru Morimoto^a, Tomoyuki Horiguchi^b, Kuriko Yamada^a, Ken Tsutsumi^a, Hideo Kurosawa^b, Kiyomi Kakiuchi*^a
^a Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan
Fax: +81(743)726089; e-Mail: kakiuchi@ms.aist-nara.ac.jp;
^b Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

Abstract

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Abstract

The acid-catalyzed rearrangement of 3-methylenetricyclo[6.3.0.0^1.4]undecan-5-one (5), prepared via the photocycloaddition of cyclohexenone to allene, gave the triquinanes. In addition, the method was applied to the synthesis of (±)-pentalenene.

Keywords

rearrangement - allene - cyclohexenone - total synthesis - pentalenene

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References

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