Development of radical addition–cyclization–elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

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• 作者：Okiko Miyata ; Atsushi Shirai ; Shintaro Yoshino ; Toshiki Nakabayashi ; Yoshifumi Takeda ; Toshiko Kiguchi ; Daisuke Fukumoto ; Masafumi Ueda ; Takeaki Naito
• 关键词：Radical reaction ; Martinelline ; Pyrroloquinoline ; Oxime ether ; α ; β ; -unsaturated ester
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：1 October 2007
• 卷：63
• 期：40
• 页码：10092-10117
• 文件大小：804 K

摘要

Radical addition–cyclization–elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu₃SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu₃SnNMe₂, Bu₃SnD, and/or D₂O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.