AI Article Synopsis
- Hyperjapones A-E and hyperjaponols A-C are complex natural compounds derived from aromatic polyketides and terpenes, found in Hypericum japonicum.
- Using a biomimetic approach, researchers synthesized hyperjapones A-E through an oxidative reaction that combines specific natural products.
- The synthesis of hyperjaponol C was successfully achieved in just four steps by mimicking its proposed biosynthetic pathway, which involves multiple transformations like epoxidation and alkene cyclization.
Article 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 hyperjaponol C to be completed in which six carbon-carbon bonds, six stereocenters, and three rings were constructed in just four steps.
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| http://dx.doi.org/10.1002/anie.201606091 | DOI Listing |
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