Lam, H.Phan, Q.Sumby, C.George, J.2018-11-082018-11-082018Australian Journal of Chemistry, 2018; 71(9):649-6540004-94251445-0038http://hdl.handle.net/2440/115905Published online: 6 July 2018Hyperjapones 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.enJournal compilation © CSIRO 2018Journal article003009723010.1071/CH181410004455252000042-s2.0-85052798072436660Sumby, C. [0000-0002-9713-9599]George, J. [0000-0002-7330-2160]