Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 1, Pages 82-86Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01003k
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Funding
- Recruitment Program of Global Experts (1000 Talents Plan)
- Gansu Province Science Foundation for Distinguished Young Scholars [20JR5RA304]
- Fundamental Research Funds for the Central Universities [lzujbky-2019-ct08]
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An unprecedented palladium(II)-catalyzed ortho-alkylation of N-methoxybenzamide with epoxides was utilized in the total synthesis of the isochroman natural product (-)-berkelic acid. By combining this strategy with a well-documented spiroacetalization cascade reaction, (-)-berkelic acid was obtained with an overall yield of 13.9% and the longest linear sequence of 11 steps. Preliminary biological studies on the synthesized natural product and its analogues were also conducted.
An unprecedented palladium(II)-catalyzed ortho-alkylation of N-methoxybenzamide with epoxides has been applied to the total synthesis of the isochroman natural product (-)-berkelic acid. Combining this strategy with a well documented spiroacetalization cascade reaction, (-)-berkelic acid is obtained in 13.9% overall yield with the longest linear sequence of 11 steps. The results of preliminary biological studies on the synthesized natural product and its analogues are also reported.
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