Biomimetic Synthesis Enables the Structure Revision of Littordials E and F and Drychampone B
Tomás Vieira de Castro1, Oussama Yahiaoui1, Ricardo A Peralta1
1Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.
Abstract:
Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an o-quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.
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