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Synthesis 2023; 55(20): 3297-3302
DOI: 10.1055/s-0041-1738443
DOI: 10.1055/s-0041-1738443
paper
Synthesis of Naturally Racemic Marilines B & C through Multicomponent Reactions Involving ortho-Quinone Methides and Various Nitrogen Nucleophiles
The authors are appreciative of the financial support provided by the Faculty Senate, the Dean of the College of Letters and Science, and the Department of Chemistry and Biochemistry at the University of California, Santa Barbara.
Abstract
Herein, we report the first total synthesis of (±)-marilines B and C, as well as a failed approach to (±)-mariline A, by using our recently developed multicomponent reaction method, which involves the interception of ortho-quinone methides with various nitrogen nucleophiles to allow easy assembly of various benzylic amine cores with diverse substituents.
Key words
ortho-quinone methides - marilines - imines - dihydrooxazoles - anilines - isoindolin-1-ones - phthalimidines - salicylaldehydesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738443.
- Supporting Information
Publication History
Received: 08 April 2023
Accepted after revision: 15 May 2023
Article published online:
28 June 2023
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For selected reviews on the applications of ortho-quinone methides in total synthesis, see: