ADVERTISEMENT
2 /3 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Cyclization In Close Quarters

March 24, 2008 | APPEARED IN VOLUME 86, ISSUE 12

R=tert-butyidimethylsilyl

The Diels-Alder reaction, a widely used transformation in organic synthesis, forms six-membered rings from a conjugated diene and a dienophile-frequently an alkene. Usually, these two reactants must be activated by catalysts or have complementary electronic properties to participate in the reaction. Phil S. Baran, Thomas J. Maimone, and Ana-Florina Voica of Scripps Research Institute have observed a catalyst-free Diels-Alder reaction between simple, nonactivated reactants at room temperature while synthesizing an intermediate en route to vinigrol, a natural product with antihypertensive and other biological activities (Angew. Chem. Int. Ed., DOI: 10.1002/anie.200800167). Vinigrol has a unique three-ring skeleton, which the team formed by strategically breaking a bond in a four-ring intermediate. The Diels-Alder reaction (shown) forms the four-ring intermediate from a bicyclic precursor. The team believes that the precursor's compact structure brings the reacting diene and alkene into proximity and promotes the cyclization. The rigidity of the resulting four-ring intermediate likely aids the subsequent bond-breaking step that forms vinigrol's three-ring skeleton, the authors write. They now hope to complete the synthesis of vinigrol from this skeleton.

X

Article:

This article has been sent to the following recipient:

Leave A Comment

*Required to comment