Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 2, Pages 429-440Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja067083p
Keywords
-
Categories
Ask authors/readers for more resources
In this article, the total syntheses of the antibiotic abyssomicin C (1) and its biologically inactive sibling abyssomicin D (3) are described. A number of unforseen roadblocks in our synthetic plan encouraged innovation, which culminated in the discovery of a new Lewis acid-templated Diels-Alder reaction. En route to abyssomicin C, we prepared and characterized its stable conformational isomer atrop-abyssomicin C (57), which in the presence of a strong acid underwent an unusual interconversion with the targeted natural product. Close inspection of the X-ray crystallographic structures of these compounds led to hypotheses on the mechanism of their interconversion. Attempted reduction of both atropisomers revealed that atrop-abyssomicin C afforded abyssomicin D much more readily, suggesting that this previously unknown atropisomer may be synthesized by the host organism and serves as a direct precursor of abyssomicin D. Finally, to gain insight into the mechanism of antiobiotic activity, several synthetic intermediates and designed analogues were evaluated for biological activity.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available