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タイトル: Synthetic Studies towards Communesins: Diastereoselective Oxidative Rearrangement of Aurantioclavine Derivatives
著者: Suetsugu, Satoshi
Tsukano, Chihiro  kyouindb  KAKEN_id
Takemoto, Yoshiji
著者名の別形: 末次, 聖
塚野, 千尋
竹本, 佳司
キーワード: Alkaloids
Heterocycles
Rearrangement
Cyclization
Diastereoselectivity
発行日: Jan-2016
出版者: Wiley-VCH Verlag
誌名: European Journal of Organic Chemistry
巻: 2016
号: 1
開始ページ: 108
終了ページ: 115
抄録: Communesins are a class of heptacyclic indole alkaloids that contain two aminal moieties and two contiguous quaternary carbon centers. We have investigated the construction of the pentacyclic skeleton of the communesins by employing the oxidative rearrangement of aurantioclavine derivatives, which are believed to be biosynthetic intermediates of the polycyclic communesin alkaloids. The quaternary C-7 carbon center was constructed in a stereoselective manner, whereas the installation of the C-11 stereocenter requires an epimerization process. The isolation of a 2-ethoxyindolenine prior to the reduction of the nitro group and cyclization steps was critical to the success of this strategy. The pentacyclic skeleton of the communesins has been prepared by the oxidative rearrangement of aurantioclavine derivatives, which are believed to be biosynthetic intermediates of the communesin alkaloids. The quaternary C-7 carbon center was constructed in a stereoselective manner, and the isolation of a 2-ethoxyindolenine intermediate was critical to the success of the strategy.
著作権等: This is the peer reviewed version of the following article: Suetsugu Satoshi, Tsukano Chihiro, Takemoto Yoshiji, Synthetic Studies towards Communesins: Diastereoselective Oxidative Rearrangement of Aurantioclavine Derivatives, European Journal of Organic Chemistry, 2016, 1, (108-115), (2016) which has been published in final form at https://doi.org/10.1002/ejoc.201501194. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/235943
DOI(出版社版): 10.1002/ejoc.201501194
出現コレクション:学術雑誌掲載論文等

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