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Type: Journal article
Title: Biomimetic total synthesis of hyperjapones A–E and hyperjaponols A and C
Author: Lam, H.
Spence, J.
George, J.
Citation: Angewandte Chemie - International Edition, 2016; 55(35):10368-10371
Publisher: Wiley
Issue Date: 2016
ISSN: 1433-7851
Statement of
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
RMID: 0030051344
DOI: 10.1002/anie.201606091
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Appears in Collections:Physics publications

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