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Synfacts 2021; 17(02): 0121
DOI: 10.1055/s-0040-1719297
DOI: 10.1055/s-0040-1719297
Synthesis of Natural Products and Potential Drugs
Synthesis of (+)-Haperforin G
Zhang W,
Zhang Z,
Tang J.-C,
Che J.-T,
Zhang H.-Y,
Chen J.-H,
*,
Yang Z.
*
Peking University and Peking University Shenzhen Graduate School, P. R. of China
Total Synthesis of (+)-Haperforin G.
J. Am. Chem. Soc. 2020;
142: 19487-19492
DOI: 10.1021/jacs.0c10122.
Total Synthesis of (+)-Haperforin G.
J. Am. Chem. Soc. 2020;
142: 19487-19492
DOI: 10.1021/jacs.0c10122.
Key words
(+)-haperforin G - limonoids - tetranortriterpenoids - ring-closing metathesis - Pauson–Khand reaction - light-mediated radical coupling - aldol addition
Significance
Chen, Yang, and co-workers report the first total synthesis of (+)-haperforin G, a structurally complex member of the limonoid family of tetranortriterpenoid natural products. Their synthesis features an efficient radical coupling of two fragments.
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Comment
Intermediate G is accessed from A in nine steps and transformed to H via a Pauson–Khand reaction. Further six steps give rise to I, which is then joined with M via a light-mediated radical-based coupling to obtain O.
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Publication History
Article published online:
20 January 2021
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