Total synthesis and structural reassignment of garcinielliptone FC, a polycyclic polyprenylated acylphloroglucinol with diverse bioactivity

Abstract

Garcinielliptone FC (GFC) was assigned to be a type A polycyclic polyprenylated acylphloroglucinol (PPAP) and was found to exhibit diverse biological activities. Now we revise the structure of GFC to...

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

“…We have had a long-standing interest in confirming or correcting proposed structures of natural PPAPs and have corrected the structures of dozens of them, ,,− so we decided to reinvestigate the assigned structures of UF, UG, AE, AF, UK, UO, and SA–SD. First, we reisolated furan-fused PPAPs UG, AE, and AF from Hypericum patulum .…”

“…For example, we recently used NMR and total synthesis to show that garcinielliptone FC, 6,7 a PPAP widely studied for its diverse bioactivity that was originally proposed to be type A, was actually the well-known type B PPAP xanthochymol. 8…”

“…It is understandable, then, that some researchers still mistake a type A PPAP for a type B one and vice versa. For example, we recently used NMR and total synthesis to show that garcinielliptone FC, , a PPAP widely studied for its diverse bioactivity that was originally proposed to be type A, was actually the well-known type B PPAP xanthochymol …”

Sequential Dieckmann cyclization enables the total synthesis of 7-epi-clusianone and 18-hydroxy-7-epi-clusianone

“…[27][28][29][30] Fortunately, replacing 2-methyl-2-butene with more reactive isobutylene led to the successful completion of Organic & Biomolecular Chemistry Paper the cross-metathesis, yielding the fully prenylated bicyclo [3.3.1]nonane 4 in 85% brsm yield. 45 With the successful synthesis of key intermediate 4, we moved on to the endgame of the total synthesis of 7-epi-clusianone (1) and 18-hydroxy-7-epi-clusianone (2). With triethylamine as the appropriate base, the benzoylation of compound 4 with benzoyl cyanide at the C-3 position occurred smoothly, thus completing the total synthesis of 7-epi-clusianone (1).…”

“…27–30 Fortunately, replacing 2-methyl-2-butene with more reactive isobutylene led to the successful completion of the cross-metathesis, yielding the fully prenylated bicyclo[3.3.1]nonane 4 in 85% brsm yield. 45…”