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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.


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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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