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Synfacts 2018; 14(10): 1001
DOI: 10.1055/s-0037-1610894
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Synthesis of (+)-Aplysiasecosterol A

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Lu Z. Zhang X. Guo Z. Chen Y. Mu T. Li A. * Shanghai Institute of Organic Chemistry, P. R. of China
Total Synthesis of Aplysiasecosterol A.

J. Am. Chem. Soc. 2018;
140: 9211-9218
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Further Information

Publication History

Publication Date:
17 September 2018 (online)

 
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Key words

(+)-aplysiasecosterol A - Hara–Roush allylation - Zweifel–Evans olefination - HAT-based radical cyclization - desymmetrization

Significance

The first total synthesis of (+)-aplysiasecosterol A is reported by Li and co-workers in 14 steps (longest linear sequence). Key features include an iron-mediated HAT radical cyclization, an asymmetric allylation, and a Zweifel–Evans olefination.


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Comment

Recognition of hidden symmetry in the core of the target structure allowed the clever application of a desymmetrization strategy starting from achiral dione A. Advanced intermediate P was assembled from bromide H and aldehyde O. Radical cyclization and deprotection led to the natural product.


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