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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Synthesis and Configuration Assignment of (+)-Myxoquaterine-450
Johanna Löhr1, Sabrina Ortmann1, Alexander Popoff2
1Technische Universität München, School of Natural Sciences, Department of Chemistry and Catalysis Research Center, Lichtenbergstrasse 4, 85747, Garching, Germany.
Abstract:
Myxoquaterines represent a recently discovered class of natural products with intriguing biological properties. They were isolated from Pendulasporacea albinea MSr 11954 and display a unique structure combining heterocyclic (pyrrole, oxazoline), hexaene, and 2-amino-1,3-diol subunits. We have now synthesized the first example of a myxoquaterine natural product, myxoquaterine-450, in a highly convergent fashion, in which the sensitive hexaene unit was established in the final stages of the synthesis (16 linear steps starting from l-serine). Comparison of the synthetic material with an authentic sample allowed to establish and confirm the constitution and configuration of the natural product.
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