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|Title:||Biomimetic total synthesis of hyperjapones A–E and hyperjaponols A and C|
|Citation:||Angewandte Chemie - International Edition, 2016; 55(35):10368-10371|
|Hiu C. Lam, Justin T. J. Spence and Jonathan H. George|
|Abstract:||Hyperjapones A–E and hyperjaponols A–C are complex natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A–E using a biomimetic, oxidative hetero-Diels–Alder reaction to couple together dearomatized acylphloroglucinol and cyclic terpene natural products. Hyperjapone A is proposed to be the biosynthetic precursor of hyperjaponol C through a sequence of: 1) epoxidation; 2) acid-catalyzed epoxide ring-opening; and 3)a concerted, asynchronous alkene cyclization and 1,2-alkyl shift of a tertiary carbocation. Chemical mimicry of this proposed biosynthetic sequence allowed a concise total synthesis of hyperjaponolC to be completed in which six carbon–carbon bonds, six stereocenters, and three rings were constructed in just four steps.|
|Keywords:||Hypericum; Terpenes; Molecular Conformation; Stereoisomerism; Biomimetic Materials; Polyketides|
|Rights:||© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim|
|Appears in Collections:||Physics publications|
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