U-62162, a member of the manumycin family of antibiotics, has been pre
pared as a mixture of diastereoisomers and shown to contain a syn-hydr
oxy epoxide nucleus and a 1,3-syn-disposed dimethyl unit in the upper
side chain; the cornerstone of the synthetic route utilises organometa
llic addition to a monoprotected quinone epoxide-the first time this a
pproach has been successfully employed to prepare a manumycin antibiot
ic.