The macquarimicins and cochleamycins are two recently isolated classes of novel natural products which have shown good antitumor activity against P388 leukemia cells. This proposal outlines a unified synthetic strategy for the construction of all members of these two families in an asymmetric fashion with a particular focus on the most potent member: macquarimicin B. The key step in the proposal is the novel merger of two separate technologies, the Claisen rearrangement and the hydroxyl- directed ketone reduction, into a one-pot conversion of a beta-hydroxy- allyl-enol ether into a syn-1,3-diol.
| White, J D; Carter, R G; Sundermann, K F et al. (2001) Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D. J Am Chem Soc 123:5407-13 |
| White, J D; Sundermann, K F; Carter, R G (1999) Improved synthesis of epothilone B employing alkylation of an alkyne for assembly of subunits. Org Lett 1:1431-4 |
