1570098-55-3Relevant academic research and scientific papers
Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization
Boyce, Jonathan H.,Porco, John A.
, p. 7832 - 7837 (2014)
We report a stereodivergent, asymmetric total synthesis of (-)-clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework. Aim for selectivity: (-)-Clusianone was produced by a stereodivergent asymmetric total synthesis in six steps from commercial materials. The synthesis utilizes a challenging formic acid-mediated cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms.
Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
, p. 11799 - 11804 (2014/10/16)
Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone
Pepper, Henry P.,Tulip, Stephen J.,Nakano, Yuji,George, Jonathan H.
, p. 2564 - 2573 (2014/04/17)
A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.
