The progress towards the total synthesis of (ent)-MPC1001

Schuber, Paul, author
Williams, Robert M., advisor
Crans, Debbie, committee member
Finke, Richard, committee member
McNaughton, Brian, committee member
Slayden, Richard, committee member
Journal Title
Journal ISSN
Volume Title
Herein are my efforts toward the total synthesis of (ent)-MPC1001, beginning with the development of a novel asymmetric [1-3]-dipolar cycloaddition utilizing a vinyl silane and a chiral lactone template. The mechanism of the cycloaddition was investigated and the cyclized product can be elaborated in 6 steps to the A-B-C ring system of the MPC family of natural products. However, the key ring-closing metathesis reaction provided irreproducible results. Therefore, a macrolactonization was utilized to synthesize an advanced lactone derivative. Current research is focused on the elaboration of the lactone to the oxepin ring. Efforts were also focused on the development of a novel β-hydroxy-α-amino acid derivative to be used in the preparation of analogues of the natural product (ent)-MPC1001. The amino acid was efficiently prepared in six steps via a Mukaiyama aldol reaction by a chiral oxazinone and 3-bromo-4-methoxybenzaldehyde. With the dipole product and the β-hydroxyl-α-amino acid derivative in hand, efforts were focused on the coupling of the two components to afford the DKP. Research was also focused on the installation of the diaryl ether portion of (ent)-MPC1001 as well as an interesting dimerization reaction. The dimerization reaction can serve as a point of divergence to the aronotin family of natural products.
2011 Fall.
Includes bibliographical references.
Rights Access
Associated Publications