Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 7, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200198
Keywords
C-H methylation; methylated naphthalene compounds; modified eremophilanes; musizin; total synthesis
Categories
Funding
- National Natural Science Foundation of China [21877062]
- Innovative and Entrepreneurial Research Team [20182036]
- Innovative and Entrepreneurial Talent program of Jiangsu Province
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In this study, new methods for synthesizing methylated naphthalene natural products were disclosed using simple and commercially available naphthalene molecules. These methods overcome the challenges of low content in plants and lack of synthetic methods.
Natural methylated naphthalene compounds, possessing diverse biological activities, remain to be studied because of low content in plants and lacking synthetic methods. Herein, we have disclosed new approaches to methylated naphthalene natural products represented by dehydrocacalohastine and musizin from simple and commercially available naphthalene molecules with the assistance of our reported regioselective C-H methylation. The dehydrocacalohastine has been firstly synthesized from 1-bromonaphthalen-2-ol in overall 8.9% yield with 8 steps. Additionally, the solution to musizin saved 2 steps with comparative yields to previous reported route.
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