A chiral pool based approach to antipodes of α-cuparenone

Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

“…Synthesized from commercially available L-malic acid (6.70 g, 50.0 mmol) according to a literature procedure in 92 % yield (7.47 g, 46.1 mmol). [42] The analytical data matched the previously published values. 1 (S)-Dimethyl-2-methoxysuccinate (14).…”

Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids

“…Alkylation of 26 with benzyl bromide was performed according to the described procedure using Ag 2 O in EtOAc, allowing preparation of the product 27 in 94% yield. 16 Notably, silver-containing side products could be recovered in more than 90% yield aer the synthesis, which is important for large-scale preparation. Further transformations included reducing of 27 with LiAlH 4 , which gave the known diol 28 (90%).…”

“…Therefore, more reactive diiodide 29 was prepared in 91% yield by the method described previously. 16 The nal steps in the synthesis of key intermediate (S)-19 included the reaction of 29 with dimethyl malonate. This step required tedious optimization of the reaction conditions; it was found that the product 30 was formed in 80% yield if 2.5-3.5 excess of the nucleophile in reuxing THF was used.…”

Natural sesquiterpenoids

“…148 A synthetic route to both antipodes of a-cuparenone has been developed. 149 A concise and highly enantioselective synthesis of (À)-aplysin has been described. 150 A total synthesis of gomerone C 161 has permitted the revision of its relative stereochemistry, 151 and has also led to the stereochemical reassignment of gomerone B 162.…”