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August 10, 2006
ORGANIC CHEMISTRY
Efficient Ageladine A Synthesis
Route to promising anticancer agent showcases the power of biomimetic strategies
Stu Borman
An efficient new total synthesis of ageladine A, a promising anticancer agent with potent antiangiogenic activity, has been devised by Sudhir R. Shengule and Peter Karuso of Macquarie University, in Sydney, Australia (Org. Lett., DOI: 10.1021/ol061584y). "Our synthesis demonstrates the power of biomimetic strategies—taking advantage of the teachings of nature in the design of an efficient synthetic strategy," Karuso says. Steven M. Weinreb's group at Pennsylvania State University reported the first total synthesis of ageladine A earlier this year (Org. Lett. 2006, 8, 1443). But the new synthesis has many fewer steps, among other advantages. "This is a very nice, exceptionally short synthesis starting from two fundamental building blocks proposed to be involved in the biogenesis of this marine metabolite," Weinreb comments. "The key Pictet-Spengler cyclization utilized by the authors may in fact have some biogenetic relevance." The procedure should be commercially viable, opening the door to large-scale testing of the natural product and its analogs.
- Chemical & Engineering News
- ISSN 0009-2347
- Copyright © 2006 American Chemical Society
