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j.tet.2014.11.065.pdf | 300.93 kB | Adobe PDF | 見る/開く |
タイトル: | Synthesis of steroidal derivatives bearing a small ring using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement |
著者: | Arichi, Norihito https://orcid.org/0000-0003-3618-4959 (unconfirmed) Hata, Kenji Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed) Yamada, Ken-ichi Yamaoka, Yousuke Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed) |
著者名の別形: | 有地, 法人 竹本, 佳司 山田, 健一 山岡, 陽介 高須, 清誠 |
キーワード: | Steroids Cyclopropanes Cyclobutanes [2+2] Cycloaddition Ring contraction |
発行日: | 14-Jan-2015 |
出版者: | Elsevier BV |
誌名: | Tetrahedron |
巻: | 71 |
号: | 2 |
開始ページ: | 233 |
終了ページ: | 244 |
抄録: | Fixing conformation by introducing a ring structure is a common strategy in drug development. We demonstrate a synthesis that installs a small carbocyclic ring as a structurally-rigid unit in drug lead compounds. Both trans- and cis-cyclobutane rings were constructed in excellent selectivities by controlling the reaction temperature of an EtAlCl2-catalyzed [2+2] cycloaddition between a silyl enol ether and an α, β-unsaturated ester. Spirocyclopropane rings were stereospecifically formed by our previously reported ring-contraction rearrangement of fused cyclobutanols. This strategy allowed stereodivergent access to a new class of steroidal derivatives bearing a small ring. |
著作権等: | © 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ The full-text file will be made open to the public on 14 January 2017 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. 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。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/243966 |
DOI(出版社版): | 10.1016/j.tet.2014.11.065 |
出現コレクション: | 学術雑誌掲載論文等 |
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