The stereoselective syntheses of five styryllactones (−)‐goniofufurone, (−)‐goniopypyrone, (−)‐7‐ epi ‐goniofufurone, (−) ‐ crassalactone B, and (−)‐crassalactone C have been achieved in five or six longest linear steps by divergent strategies starting from chiral pool methyl α ‐D‐glucopyranoside, respectively. The key transformations include a sequential reaction of Bernet–Vasella‐type reductive elimination and nucleophilic addition in a one‐pot process and a cascade reaction of cross‐metathesis/deprotection/intramolecular oxa‐Michael addition/lactonization involving the rapid construction of the challenging dioxabicyclo3.3.0octane and dioxabicyclo3.3.1nonan‐3‐one scaffolds.
Zhang et al. (Mon,) studied this question.