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Ehrlich G, Stark CB. Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q. Org Lett. 2016;18(19):4802-4805doi: 10.1021/acs.orglett.6b02193.
Ehrlich, G., & Stark, C. B. (2016). Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q. Organic letters, 18(19), 4802-4805. https://doi.org/10.1021/acs.orglett.6b02193
Ehrlich, Gunnar, and Stark, Christian B W. "Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q." Organic letters vol. 18,19 (2016): 4802-4805. doi: https://doi.org/10.1021/acs.orglett.6b02193
Ehrlich G, Stark CB. Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q. Org Lett. 2016 Oct 07;18(19):4802-4805. doi: 10.1021/acs.orglett.6b02193. Epub 2016 Sep 16. PMID: 27636302.
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Org Lett. 2016 Oct 07;18(19):4802-4805. doi: 10.1021/acs.orglett.6b02193. Epub 2016 Sep 16.

Total Synthesis of Cytospolide D and Its Biomimetic Conversion to Cytospolides M, O, and Q.

Organic letters

Gunnar Ehrlich, Christian B W Stark

Affiliations

  1. Department of Chemistry, Institute of Organic Chemistry, University of Hamburg , Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.

PMID: 27636302 DOI: 10.1021/acs.orglett.6b02193

Abstract

A total synthesis of cytospolide D, starting from l-glutamic acid, is described. The critical macrolactonization to the 10-membered lactone containing an (E)-configured double bond was successfully achieved by Shiina esterification. Conversion of cytospolide D to its bicyclic derivatives M, O, and Q was accomplished under mild conditions, lending support to the proposed biosynthetic hypothesis.

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