1. Total synthesis of prenylated acylphloroglucinols: faberiones A, B, and E.
- Author
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Ziya Ahmad, Sarwat Asma and Khan, Faiz Ahmed
- Subjects
- *
NATURAL products , *PHLOROGLUCINOL , *BENZOPYRANS , *IODINATION , *HYPERICUM , *ACYLATION , *RING formation (Chemistry) - Abstract
The first total synthesis of acylphloroglucinol-based natural products faberiones A, B, and E is reported, which were isolated from Hypericum faberi. Total syntheses of faberiones A and B are accomplished in six linear steps from commercially accessible 1,3,5-trimethoxybenzene (methyl protected form of phloroglucinol) in overall yields of 31 and 33% respectively, via simple and straightforward approaches that include acylation, o-methoxy deprotection, selective iodination and tandem-Sonogashira cyclization followed by C-geranylation. Faberione E is achieved in two linear steps from acylphloroglucinol with an overall yield of 57% via geranylation followed by benzopyran formation reaction. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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