Stereochemical Relay via Axially Chiral Styrenes: Asymmetric Synthesis of the Antibiotic TAN‐1085

It works both ways: The transcription of two types of chirality (central⇄axial) in three chirality-transfer steps (steps A–C in the scheme; R1 and R2 are bulky groups) was exploited in the synthesis of TAN-1085. Induced by the central chirality of a sulfinyl group, the axial stereochemistry of a styrene derivative was transferred to the axial stereochemistry of a biaryl intermediate and finally to the two stereogenic centers in the aglycon of TAN-1085.