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Synfacts 2009(4): 0361-0361  
DOI: 10.1055/s-0028-1088090
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Myriocin

Contributor(s): Philip Kocienski, Stewart Eccles
M. C. Jones, S. P. Marsden*
University of Leeds, UK
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

Myriocin is a potent immunosuppressant isolated from the fungi Mycelia sterilia, Myriococcum albomyces, and Isaria sinclairii. It inhibits serine palmitoyl transferase, a key enzyme in sphingolipid biosynthesis. The key step in the synthesis shown above is the construction of the quaternary vinylglycine D via deconjugative asymmetric alkylation of the dehydroamino acid C.