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Synthesis

Aromatic Approach To (+)-Batzelladine B

Natural Product Synthesis: By using pyrrole-based starting materials, chemists develop a streamlined strategy for anti-HIV alkaloid’s synthesis

by Bethany Halford
September 21, 2015 | APPEARED IN VOLUME 93, ISSUE 37

First isolated from a Caribbean sponge 20 years ago, the batzelladine alkaloids have captured the imagination of chemists for two reasons: The compounds have powerful anti-HIV activity, and their complex structures provide an intriguing target to tackle with total synthesis. The structures are challenging to construct, however, because of their multiple basic nitrogen groups. These nucleophilic groups are prone to oxidation and tend to react in unexpected ways. Previous batzelladine syntheses that start with nonaromatic N-heterocycles have addressed this problem by using nitrogen protecting groups that require additional reaction steps to put on and remove. Yale University chemists Seth B. Herzon, Brendan T. Parr, and Christos Economou thought they could streamline one such synthesis by starting with aromatic nitrogen heterocycles, such as functionalized pyrroles, and then selectively reducing the pyrroles in the late stages of the synthetic scheme. Their efforts produced a nine-step synthesis of (+)-batzelladine B, about half as many steps as it takes to make other batzelladines (Nature 2015, DOI: 10.1038/nature14902). Using this strategy, the Yale team reports, they can use synthetic pathways that wouldn’t be viable using aliphatic nitrogen building blocks. What’s more, they say they are able to temper nitrogen’s promiscuous behavior.

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