Biomimetic synthesis enables the structure revision of littordials E and F and drychampone B
Date
2020
Authors
Vieira de Castro, T.
Yahiaoui, O.
Peralta, R.A.
Fallon, T.
Lee, V.
George, J.H.
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Organic Letters, 2020; 22(20):8161-8166
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Tomás Vieira de Castro, Oussama Yahiaoui, Ricardo A. Peralta, Thomas Fallon, Victor Lee and Jonathan H. George
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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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© 2020 American Chemical Society