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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus

IMPACT FACTOR 2018: 1.000

CiteScore 2018: 0.99

SCImago Journal Rank (SJR) 2018: 0.246
Source Normalized Impact per Paper (SNIP) 2018: 0.437

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Volume 73, Issue 1-2


Synthesis of methyl 4-dihydrotrisporate B and methyl trisporate B, morphogenetic factors of Zygomycetes fungi

Yoko Nakamura / Christian Paetz / Wilhelm Boland
  • Corresponding author
  • Max Planck Institute for Chemical Ecology, Department of Bioorganic Chemistry, Hans-Knöll-Straße 8, 07745 Jena, Germany
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Published Online: 2017-11-21 | DOI: https://doi.org/10.1515/znc-2017-0148


(9Z)-Methyl 4-dihydrotrisporate B and (9Z)-methyl trisporate B, pheromones of Zygomycetes fungi, have been synthesized using Stille cross-coupling from previously described cyclohexenone precursors. Conducting the coupling without protection groups allowed for a short and stereospecific synthesis route of the late trisporoids. Stability studies for both the compounds revealed (9Z)-methyl trisporate B to be very unstable against UV irradiation.

This article offers supplementary material which is provided at the end of the article.

Keywords: natural products; Stille cross-coupling; total synthesis; trisporoids; Zygomycetes


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About the article

Received: 2017-08-20

Revised: 2017-10-06

Accepted: 2017-10-12

Published Online: 2017-11-21

Published in Print: 2018-01-26

Citation Information: Zeitschrift für Naturforschung C, Volume 73, Issue 1-2, Pages 59–66, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2017-0148.

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