Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A.
Synthetic pathways to complex meroterpenes derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have not been reported despite heavy biosynthetic and medicinal interest. Herein we report the first total synthesis of berkeleyone A, a potential gateway compound to a plethora of fungal-derived meroterpenes, in 13 steps. In addition, we have further developed a novel annulation reaction for the synthesis of hydroxylated 1,3-cyclohexadiones in a single step.
Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
Chi P
CP
Ting
Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
Gong
G
Xu
Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
Xianhuang
X
Zeng
Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
Thomas J
TJ
Maimone
D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013729:Terpenes / Q000138:chemical synthesis*
D003512:Cyclohexanones; D013729:Terpenes; C004636:1,3-cyclohexanedione