Bruckner Sebastian, Bilitewski Ursula, Schobert Rainer
Organic Chemistry Laboratory, University Bayreuth , Universitaetsstrasse 30, 95440 Bayreuth, Germany.
Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
Org Lett. 2016 Mar 4;18(5):1136-9. doi: 10.1021/acs.orglett.6b00245. Epub 2016 Feb 12.
Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from L-tyrosine or D-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.
首次以L-酪氨酸或D-酪氨酸为起始原料，以10%的总收率合成了蜘蛛致病真菌代谢产物托鲁比罗酮D的四种立体异构体。通过（E）-选择性HWE和维蒂希烯烃化反应构建并连接了3-癸三烯酰侧链。它们对药物敏感的大肠杆菌菌株的抗菌活性有很大差异。
