Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5263847 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
The results of quantum chemical calculations on a previously proposed biosynthetic pathway for the formation of calophyline A from rhazimol, which features formally forbidden 4-electron [1,2] and [1,3] sigmatropic shifts, are discussed. The proposed pathway was not found to be energetically viable, despite a surprisingly low predicted barrier for the [1,3] shift, but an alternative route involving a series of tautomerizations and carbonyl addition reactions is shown to be more energetically feasible.
Related Topics
Physical Sciences and Engineering
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Authors
Brandi M. Hudson, Jason G. Harrison, Dean J. Tantillo,