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Synfacts 2020; 16(02): 0119
DOI: 10.1055/s-0039-1691449
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Viridin and (–)-Viridiol

Contributor(s):
Erick M. Carreira
,
Manuel Freis
Ji Y, Xin Z, He H, Gao S. * East China Normal University, Shanghai, P. R. of China
Total Synthesis of Viridin and Viridiol.

J. Am. Chem. Soc. 2019;
141: 16208-16212
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Further Information

Publication History

Publication Date:
21 January 2020 (online)

 
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Key words

(–)-viridin - (–)-viridol - furanosteroid - [3+2] cycloaddition - MHAT radical cyclization

Significance

Viridin and Viridiol belong to the class of furanosteroids and were isolated from the fungal species of Gliocladium virens and Trichoderma viride.


 

Comment

Unsaturated ester A, accessed in four steps from l-(+)-ribose, underwent intramolecular [3+2] cycloaddition after nitrile oxide formation, affording isoxazoline B. Cobalt-catalyzed MHAT radical cyclization was used to construct the steroid skeleton of G.


 

 


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