B. Schmidt, S. Audörsch
Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne
Org. Lett. 2016, 18, 1162
DOI: 10.1021/acs.orglett.6b00274
The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated (8Z, 10E)-diene moiety was achieved through a tethered ring closing metathesis approach, comprising a Ru-catalyzed RCM, followed by base-induced elimination. A Pd-catalyzed Cadiot-Chodkiewicz coupling was used for the synthesis of the diyne. Overall, atractylodemayne A was synthesized in nine steps for the longest linear sequence.
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