Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction

Autor:	Xiao-Ming Zhang, Tian Ke, Fu-Min Zhang, Qing-Bo Zhuang, Yong-Qiang Tu, Xiang Guo, Rui-Qi Si, Shuang-Hu Wang
Rok vydání:	2020
Předmět:	Indole test Bicyclic molecule 010405 organic chemistry Stereochemistry Chemistry Aspidofractinine Total synthesis General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Catalysis 0104 chemical sciences Semipinacol rearrangement Bischler–Napieralski reaction Mannich reaction
Zdroj:	Angewandte Chemie International Edition. 59:21954-21958
ISSN:	1521-3773 1433-7851
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ec810bdc124869f7b7d54ed068d388d1 https://doi.org/10.1002/anie.202009238 Zobrazit plný text záznamu Plný text