Biomimetic synthesis of hyperjapones F-I
Date
2018
Authors
Lam, H.
Phan, Q.
Sumby, C.
George, J.
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Journal article
Citation
Australian Journal of Chemistry, 2018; 71(9):649-654
Statement of Responsibility
Hiu C. Lam, Quang D. Phan, Christopher J. Sumby, and Jonathan H. George
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DOI
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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Published online: 6 July 2018
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Journal compilation © CSIRO 2018