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Synfacts 2017; 13(04): 0337
DOI: 10.1055/s-0036-1590102
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Zaragozic Acid C

Contributor(s):
Erick M. Carreira
,
Philipp Sondermann
Kawamata T. Nagatomo M. Inoue M. * The University of Tokyo, Japan
Total Synthesis of Zaragozic Acid C: Implementation of Photochemical C(sp3)–H Acylation.

J. Am. Chem. Soc. 2017;
139: 1814-1817
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Further Information

Publication History

Publication Date:
17 March 2017 (online)

 
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Key words

squalene synthase inhibitor - Norrish–Yang cyclization - squalestatins - zaragozic acid C

Significance

Zaragozic acid C is an inhibitor of mammalian squalene synthase. The family of zaragozic acids has recently regained attention due to further biological activities, e.g. as antitumor agents or as inhibitors of Ras farnesyl protein transferase and dengue virus replication.


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Comment

Gluconolactone-derived A was concisely elaborated into diketone G. An acylative sequence of a Norrish–Yang cyclization and oxidative cleavage yielded I. Acid-catalyzed rearrangement revealed the characteristic highly oxygenated bicyclic core that was further transformed into zaragozic acid C.


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