title: Concise total synthesis of (±)-actinophyllic acid.
abstract: A concise total synthesis of the complex indole alkaloid (±)-actinophyllic acid was accomplished by a sequence of reactions requiring only 10 steps from readily-available, known starting materials. The approach featured a Lewis acid-catalyzed cascade of reactions involving stabilized carbocations that delivered the tetracyclic core of the natural product in a single chemical operation. Optimal conversion of this key intermediate into (±)-actinophyllic acid required judicious selection of a protecting group strategy.
authors.affiliation: Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
authors.forename: Brett A
authors.initials: BA
authors.lastname: Granger
authors.affiliation: Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
authors.forename: Ivan T
authors.initials: IT
authors.lastname: Jewett
authors.affiliation: Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Butler
authors.affiliation: Department of Chemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA.
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
keywords: Cascade Reaction; Iminium Ion; Mannich-type Reaction; Total Synthesis