Synthesis of nonactin and the proposed structure of trilactone.
[reaction: see text] An efficient enantioselective route to nonactin using a novel beta-inversion of an Evans syn aldol to construct the THF ring is presented. Through total synthesis, the structure for trilactone proposed in the literature is shown likely to be incorrect.
Wu
Yikang
Y
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China. yikangwu@mail.sioc.ac.cn
Sun
Ya-Ping
YP
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007783:Lactones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013305:Streptomyces griseus / Q000737:chemistry
D000900:Anti-Bacterial Agents; D007783:Lactones; D018942:Macrolides; C518782:trilactone; C050476:nonactin