Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 35, Pages 10368-10371Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606091
Keywords
biomimetic synthesis; carbocation rearrangements; cascade reactions; natural products; terpenoids
Categories
Funding
- Australian Research Council [DP160103393]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available