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

• Published in: Journal of the American Chemical Society Vol. 112; no. 8; pp. 2998 - 3017
• Main Authors: Jones, Todd K, Reamer, Robert A, Desmond, Richard, Mills, Sander G
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.1990; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology

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. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of t...