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Synlett 2023; 34(10): 1087-1097
DOI: 10.1055/a-2007-9342
DOI: 10.1055/a-2007-9342
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Total Synthesis of Fused Polycyclic Alkaloids Based on Oxidative Phenolic Couplings and Aza-Michael Reactions
This research was funded by the Japan Society for the Promotion of Science (JSPS), Grants-in-Aid for Scientific Research on Innovative Areas ‘Advanced Molecular Transformations by Organocatalysts’ (Grant nos. 23105013 to K.N.) and ‘Middle Molecular Strategy’ (18H04387 to K.N.), and the JSPS, Grants-in-Aid for Scientific Research (B) (17H03052 to K.N.). M.O. is grateful to the JSPS, KAKENHI (Grant Nos. 18K14210 and 20K05488).
Abstract
Alkaloids with fused polycyclic frameworks are attractive targets for synthetic organic chemists because of their structural complexity and biological activities, and a variety of strategies for their synthesis have been developed. Herein, we describe our strategy of utilizing oxidative phenolic coupling and a regioselective intramolecular aza-Michael reaction to generate fused polycyclic structural frameworks, and its application for the total syntheses of (+)-gracilamine and various hasubanan alkaloids.
1 Introduction
2 Total Synthesis of (+)-Gracilamine
3 Synthetic Studies on Monoterpene Indole Alkaloids
4 Total Synthesis of Hasubanan Alkaloids
5 Summary
Key words
oxidative phenolic coupling - aza-Michael reaction - hypervalent iodine - total synthesis - fused polycyclic alkaloidsPublication History
Received: 18 December 2022
Accepted after revision: 04 January 2023
Accepted Manuscript online:
04 January 2023
Article published online:
09 February 2023
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