Total synthesis of (±)-γ-indomycinone

Abstract The total synthesis of racemic γ-indomycinone has been achieved following an innovating convergent approach. The key step in the construction of the tetracyclic core corresponds to a Diels–Alder reaction between a substituted 5-isoprenyl-3,4-dihydro-2 H -pyran and juglone as the dienophile. The used strategy can easily be transposed to the synthesis of ( R )-γ-indomycinone starting from optically pure (2 R )-2-benzyloxy-2-methylbutanal.