Total Synthesis and Configuration Assignment of (+)-Myxoquaterine-450

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.

Keywords: amino alcohols; cross-coupling; natural products; structure elucidation; total synthesis.