New synthetic strategy for the preparation of linear phenolic natural products

Organic acid induced olefination reaction of lactones

“…On the other hand, by the Reformatsky reaction of isochromen-1-one derivatives, 1-naphthol derivatives as major products are formed. 20 Therefore, this finding supports that lactone ring-opening in the tetrahedral intermediate hardly occurs during the present olefination. Heterocycle-fused lactones are also suitable substrates.…”

Inhibition of Hsp90 with Resorcylic Acid Macrolactones: Synthesis and Binding Studies

“…[42] In order to circumvent the formation of decomposition products, it was reasoned that use of the dianion from an ortho-toluic acid instead of the ester-derived monoanion might be preferable, since such dianions have been successfully used in synthesis previously. [43][44][45][46] Thus the corresponding toluic acid 12 [47] was treated with 2.2 equivalents of sec-butyllithium. Quenching the resulting dilithiated toluate with the Weinreb amide 9 resulted in a mixture of starting acid 12 and acylated material after The PMB-protecting group could be removed oxidatively from macrocycle 14 using cerium(IV) ammonium nitrate (CAN) to give allyl alcohol 15 in reasonable yield (Scheme 4), ready for conversion into other substituents.…”

Biomimetic syntheses of polyketide aromatics from reaction of an orsellinate anion with pyrones and a pyrylium salt

“…When (34) was heated with NaOH in aqueous methanol followed by treatment with hydrogen chloride a single product was observed. This was alternariol dimethyl ether (36) (83% yield), which on demethylation with hydriodic acid according to the published procedure l o gave alternariol (6).…”