Synthesis of the C-8-C-24 Fragment of Maltepolide C by Using a Tandem Di­hydroxylation/SN2 Cyclization Sequence

A highly stereoselective synthesis of the C‐8–C‐24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key step. Other important steps include a Crimmins‐modified Evans aldol reaction, a Brown asymmetric allylation, a Horner–Wadsworth–Emmons olefination, and a Corey–Bakshi–Shibata (CBS) reduction. A highly stereoselective synthesis of the C‐8–C‐24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key step.