cis-Decalins from Quinic Acid: Toward a Synthesis of Branimycin

Marchart, Stefan; Mulzer, Johann; Enev, Valentin S.   

Organic Letters  (2007),  9(5),  813-816.

Starting from (−)-quinic acid an efficient synthesis of highly functionalized cis-α,β-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions:  a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.