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The total synthesis of strobilurin B

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Abstract

A new regio- and stereocontrolled total synthesis of the antibiotic strobilurin B is performed in nine steps in 5.5% overall yield.

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Correspondence to N. Ya. Grigorieva.

Additional information

On the occasion of the 80th anniversary of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences. For the preliminary communication, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0491–0496, February, 2014.

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Popovsky, V.A., Stepanov, A.V. & Grigorieva, N.Y. The total synthesis of strobilurin B. Russ Chem Bull 63, 491–496 (2014). https://doi.org/10.1007/s11172-014-0458-1

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  • DOI: https://doi.org/10.1007/s11172-014-0458-1

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