A Concise Total Synthesis of (+)‐Neopeltolide

Application of catalytic Z-selective olefin metathesis in natural product synthesis

“…19 Its potent antiproliferative activity against various human cancer cell lines has attracted the attention of the synthesis community over the past years. [20][21][22][23] Recently, Hoveyda and coworkers reported the shortest synthesis to date with 28 steps employing four different Z-selective OM reactions (Scheme 8). 24…”

“…However, high catalyst loadings of 20-30 mol% and elevated temperatures of 80-100 °C were required to obtain lactone 32 in yields of 74-85%. 20 (Table 2). Within three hours, it afforded the macrocyclic alkene 32 with excellent Zselectivity at ambient temperature.…”

Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs

“…[17] After protection group adjustment, DBU-promoted intramolecular oxa-conjugate addition of 65 afforded compound 66 in 73% yield (d.r. >20:1).…”

The intramolecular oxa-Michael reaction for tetrahydropyran formation : mechanism and synthesis

“…Lewis bases have been reported to promote the carbomethoxylation reactions of epoxides. 59 Carbonylation of enantiomerically enriched epoxide in the presence of DMAP catalyst under almost identical conditions that was applied in the previous experiments gave the desired β-hydroxy-ester product 68 in excellent yield (97%) (Figure 33.). 60 The reaction was conducted in ethanol at RT using freshly sublimed catalyst under 7 bar CO pressure.…”

“…Soon afterwards, Fuwa et al showcased a regioselective cross-metathesis of a selectively protected diene-1,3-diol in the synthesis of (+)-Neopeltolide. 59 They found that the protection of the allylic alcohol was indispensable for the successful regioselective replacement ( Figure 113). Doing so, the two double bonds were sufficiently differentiated to furnish the desired enal product 34.…”