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Total Synthesis of Metaphanine and Oxoepistephamiersine
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2023-08-21 , DOI: 10.1002/anie.202310917
Ya-Kui Sun 1 , Jin-Bao Qiao 1 , Yu-Meng Xin 1 , Qin Zhou 1 , Zhi-Hua Ma 1 , Hui Shao 1 , Yu-Ming Zhao 1
Affiliation  

Two complex hasubanan alkaloids were synthesized from inexpensive cyclohexanedione monoethylene acetal by a divergent route featuring a palladium-catalyzed cascade cyclization. Regioselective Baeyer–Villiger oxidation followed by MeNH2-triggered skeletal reorganization formed the benzannulated aza[4.4.3]propellane, and late-stage regio- and diastereoselective oxidative annulation of a sp3 C−H bond formed the challenging tetrahydrofuran ring system.

中文翻译:

Metaphanine 和 Oxoepistephamiersine 的全合成

通过钯催化级联环化的不同路线,由廉价的环己二酮单乙烯缩醛合成了两种复杂的哈苏巴南生物碱。区域选择性Baeyer-Villiger氧化随后MeNH 2触发的骨架重组形成了苯并环氮杂[4.4.3]丙烷,而sp 3 C−H键的后期区域和非对映选择性氧化环形成了具有挑战性的四氢呋喃环系统。
更新日期:2023-08-21
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