Total synthesis and structural revision of (+/-)-tricholomalides A and B.
The neurotrophic diterpenoids, tricholomalides A and B, were synthesized in a concise fashion. Key transformations include a ketene [2 + 2] cycloaddition and a Grignard-type reaction. In the course of the synthesis, it was determined that the structures of tricholomalides A and B had originally been misassigned.
Wang
Zhang
Z
Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA.
Min
Sun-Joon
SJ
Danishefsky
Samuel J
SJ
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; D005030:Ethylenes; D007659:Ketones; C482765:tricholomalide A; C482766:tricholomalide B; C008223:ketene