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Synfacts 2016; 12(07): 0659
DOI: 10.1055/s-0035-1562297
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (−)-Rubriflordilactone B

Contributor(s):
Erick M. Carreira
,
Johannes Boshkow
Yang P, Yao M, Li J, Li Y, Li A * Shanghai Institute of Organic Chemistry, P. R. of China
Total Synthesis of Rubriflordilactone B.

Angew. Chem. Int. Ed. 2016;
55: 6964-6968
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Further Information

Publication History

Publication Date:
17 June 2016 (online)

 
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Key words

(−)-rubriflordilac-tone B - Schisandraceae bisnortriterpenoid - Sonogashira cross-coupling - oxidative 6π-electrocyclization

Significance

Li and co-workers report the first total synthesis of (−)-rubriflordilactone B. They obtained the Schisandraceae triterpenoid in a convergent approach by retrosynthetic cleavage of the aromatic ring.


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Comment

Fragments F and K were joined by a Sonogoshira cross-coupling. Hydrosilylation with Karstedt’s catalyst was then followed by 6π-electrocyclization and oxidation to form the aromatic ring, fusing the fragments of the natural product.


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