Chemistry of tricarbonyl hemiketals and application of Evans' technology to the total synthesis of the immunosuppressant (-)-FK-506

Article abstract of DOI:10.1021/ja00164a023

Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Application of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C₁₀-C₁₈ fragment and to improvements in the preparation of the C₂₀-C₃₄ segment are also discussed.