Asperazine is a compound that has recently been isolated from a sponge that lives in the Carribbean Sea. Asperazine has only been isolated one time in small amounts, but from the minute quantities available, biological testing indicated that asperazine exhibited both high potency and selectivity for destroying leukemia cells. The combination of its impressive initial biological activity, scarcity in nature, and complex chemical structure makes asperazine an attractive candidate for total synthesis. In addition to synthesizing asperazine itself, this synthetic route will allow for the synthesis of a substantial number of analogues for the purpose of developing a structure-activity relationship (SAR). The synthetic route is outlined herein. Key steps will include a catalytic, diastereoselective Heck reaction to set a crowded quaternary center, and an Overman rearrangement to ultimately generate an amino acid functional group. This proposed route is concise and involves novel applications of the Heck reaction and Overman rearrangement. This synthesis will supply valuable material to aid in the development of potential anticancer agents.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32GM020589-02
Application #
6385209
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Marino, Pamela
Project Start
2001-04-07
Project End
Budget Start
2001-04-07
Budget End
2002-04-06
Support Year
2
Fiscal Year
2001
Total Cost
$34,832
Indirect Cost
Name
University of California Irvine
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
161202122
City
Irvine
State
CA
Country
United States
Zip Code
92697