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RESEARCH ARTICLE
Contents Vol 71(9)

Biomimetic Synthesis of Hyperjapones F-I

Hiu C. Lam A , Quang D. Phan A , Christopher J. Sumby A and Jonathan H. George A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.

B Corresponding author. Email: jonathan.george@adelaide.edu.au

Australian Journal of Chemistry 71(9) 649-654 https://doi.org/10.1071/CH18141
Submitted: 7 April 2018  Accepted: 3 May 2018   Published: 6 July 2018

Abstract

Hyperjapones F–I are tetracyclic meroterpenoids recently isolated from Hypericum japonicum. All four of these natural products have been synthesised using oxidative, intermolecular hetero-Diels–Alder reactions to couple their common biosynthetic precursor, norflavesone, to the appropriate monoterpene building blocks: sabinene, β-pinene, and α-pinene. The synthesis of enantiomerically pure hyperjapones H and I and comparison of their optical rotations to those of the natural samples indicated that these meroterpenoids are probably biosynthesised as either racemic or scalemic mixtures.


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