Syntheses of anacardic acids and ginkgoic acid

Enantioselective Butenolide Preparation for Straightforward Asymmetric Syntheses of γ‐Lactones – Paraconic Acids, Avenaciolide, and Hydroxylated Eleutherol

“…The sequence comprises only two steps: firstly, a dehydration of butanolide R , R ‐ 3e with MsCl/NEt 3 to give butenolide R ‐ 20e (90 % ee ), and secondly a Hauser–Kraus annulation23 initiated by the Michael addition of deprotonated (phenylsulfanyl)phthalide 19 24 to R ‐ 20e . The phthalide was prepared from the amide 17 25 in two steps 26. Unlike in the literature,24 we used dimsyl‐Li (in 3:2 THF/DMSO) for deprotonation of this phthalide.…”

Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative

“…Several syntheses of anacardic acid have been described so far; however these routes require harsh conditions that are not compatible with many functional groups. [24][25][26] Therefore, a new synthetic route was developed, in which a Sonogashira coupling is the key step (Scheme 1).…”

Stereoselective Synthesis of the Monomeric Unit of SCH 351448

“…The methyl ester 2, which was chosen as a synthetic equivalent for the seco acid, could be assembled from three building blocks: the phosphonium salt 3, [5] the aldehyde 4, and the ketone 5 (Scheme 1). First, a Wittig reaction between 3 and 4 was devised for the formation of the C21-C22 bond.…”

“…[4] Here, we report our results on an efficient, stereoselective synthesis of the monomeric unit of SCH 351448.(Scheme 2). Lithiation of 6 and subsequent treatment with an excess of methyl chloroformate gave the benzylchloride 7, [5] which was converted into the phosphonium salt 3. Scheme 2. a) nBuLi, 5.5 equiv.…”

“…(Scheme 2). Lithiation of 6 and subsequent treatment with an excess of methyl chloroformate gave the benzylchloride 7, [5] which was converted into the phosphonium salt 3. Scheme 2. a) nBuLi, 5.5 equiv.…”