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

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Nakamura,  Yoko
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Paetz,  Christian
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Boland,  Wilhelm
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Nakamura, Y., Paetz, C., & Boland, W. (2018). Synthesis of methyl 4-dihydrotrisporate B and methyl trisporate B, morphogenetic factors of Zygomycetes fungi. Zeitschrift für Naturforschung, C: Journal of Biosciences, 73(1), 59-66. doi:10.1515/znc-2017-0148.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002D-FF96-6
Abstract
(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.