A Desymmetrization Approach toward Highly Oxygenated cis-Decalins

Gromov, Alexey; Enev, Valentin; Mulzer, Johann.   

Organic Letters  (2009),  11(13),  2884-2886. 

The cis-decalin core 2 of the antibiotic branimycin has been prepared by desymmetrization of diepoxynaphthalene 4. The key steps involve two successive SN′ opening of the oxa-bridges. An improved procedure for the synthesis of 4 is also described.