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Synfacts 2019; 15(05): 0463
DOI: 10.1055/s-0037-1612456
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (–)-Vinigrol

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Yu X, Xiao L, Wang Z, Luo T. * Peking University, P. R. of China
Scalable Total Synthesis of (–)-Vinigrol.

J. Am. Chem. Soc. 2019;
141: 3440-3443
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Further Information

Publication History

Publication Date:
15 April 2019 (online)

 
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Key words

(–)-vinigrol - Cope rearrangement - Zweifel olefination - Diels–Alder reaction

Significance

The authors report the total synthesis of (–)-vinigrol, which has been an attractive target since its isolation in 1987. Key features of the synthesis include a transannular Diels–Alder reaction and an anionic Cope rearrangement.


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Comment

The synthesis starts from (–)-limonene and gives ketone B following a known procedure. Anionic Cope rearrangement and further elaboration yield macrocycle H. Intramolecular Diels–Alder reaction gives access to the skeleton of vinigrol, which itself is obtained after five more steps.


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