Synthesis of an Advanced Precursor of Demethoxyviridin

Abstract

The synthesis of a potential precursor 3 to demethoxyviridin (1b) is described. The centerpiece of this strategy was the conversion of the previously described dibromoolefin 6 to the masked alkyne β-hydroxyaldehyde 5 in a single step. Further elaboration then produced the alkyne oxazole 4, which on thermolysis, followed by in situ tautomerization and silylation, led directly to 3.

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GRAPHICAL ABSTRACT

Keywords:

• Demethoxyviridin
• Diels–Alder/retro-Diels–Alder reaction
• furanosteroids
• Stille coupling