Date of Graduation
A 3-step method for the preparation of 2-methyl-l,3-syn diols was developed and demonstrated on several examples. A previous incarnation of this method was used in the formal synthesis of two polyoxygenated natural products. RK-397 is a 32-membered oxopolyene macrolide antibiotic which also exhibits anti-cancer activity. Virginiamycin M2 (also known as flavofungin I) is a member of the streptogramin antibiotic family which are active against vancomycin-resistant s. aureus. The methodology employed for setting many of the stereocenters in these two products is asymmetric catalysis. This allows for either enantiomer to be created and also is efficient by means of chirality multiplication.
Mortensen, Matthew S., "Synthesis of polyol natural products: Applications to RK-397 and Virginiamycin." (2007). Graduate Theses, Dissertations, and Problem Reports. 9455.