Stereo flexible synthesis of the C8–C23 fragment of antarlides, androgen receptor antagonists†

Abstract

A practical and efficient synthesis of the C8–C23 fragment of antarlides A–H, incorporating six stereocenters and a conjugated diene, is reported. A strategic combination of synthetic methods, including CBS reduction, Evans’ aldol reaction, Keck–Maruoka allylation, and enzymatic resolution, enabled the selective introduction of these stereocenters. Furthermore, the pivotal coupling of key fragments is successfully executed through a Julia–Kocienski olefination reaction, connecting the C8–C14 and C15–C23 subunits.