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Title: Synthesis of steroidal derivatives bearing a small ring using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement
Authors: Arichi, Norihito
Hata, Kenji
Takemoto, Yoshiji
Yamada, Ken-ichi
Yamaoka, Yousuke
Takasu, Kiyosei
Author's alias: 有地, 法人
竹本, 佳司
山田, 健一
山岡, 陽介
高須, 清誠
Keywords: Steroids
Cyclopropanes
Cyclobutanes
[2+2] Cycloaddition
Ring contraction
Issue Date: 14-Jan-2015
Publisher: Elsevier BV
Journal title: Tetrahedron
Volume: 71
Issue: 2
Start page: 233
End page: 244
Abstract: 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.
Rights: © 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'.
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/2433/243966
DOI(Published Version): 10.1016/j.tet.2014.11.065
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