Tetrahedron

A novel total synthesis of isocryptolepine based on a microwave-assisted tandem Curtius rearrangement and aza-electrocyclic reaction

…, A Oda, R Yoshinaga, N Hatae, M Ishikura, S Hibino

Index: Hayashi, Kaori; Choshi, Tominari; Chikaraishi, Kyoko; Oda, Aimi; Yoshinaga, Rikako; Hatae, Noriyuki; Ishikura, Minoru; Hibino, Satoshi Tetrahedron, 2012 , vol. 68, # 22 p. 4274 - 4279

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Citation Number: 21

Abstract

A new entry to the total synthesis of isocryptolepine (cryptosanguinolentine), isolated from Cryptolepis sanguinolenta, was achieved by constructing a tetracyclic ring system through a microwave-assisted tandem Curtius rearrangement and electrocyclic reaction of an aza 6π- electron system. The tetracyclic lactam was converted to isocryptolepine in a four-step sequence.

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