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- Title
Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction.
- Authors
Wang, Shuang‐Hu; Si, Rui‐Qi; Zhuang, Qing‐Bo; Guo, Xiang; Ke, Tian; Zhang, Xiao‐Ming; Zhang, Fu‐Min; Tu, Yong‐Qiang
- Abstract
A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.
- Subjects
REARRANGEMENTS (Chemistry); INDOLE alkaloids; MANNICH reaction; INDOLE; HEPTANE
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 49, p22138
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202009238