Synthesis of the Decalin Subunit of Coloradocin

✍ Scribed by Edda Gössinger; Alexander Schwartz; Natascha Sereinig

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 190 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00111-3

✦ Synopsis

AbstractÐThe cis-decalin subunit of coloradocin is synthesized starting with an intermediate of our synthetic attempts towards nodusmicin. After transforming the additional functionalities of this tetracyclic b-diketal reductive cleavage with SmI 2 leads to a tricyclic diketone. Selective reduction is followed by acidic fragmentation to the desired cis-decalin derivative. The very mild conditions of this fragmentation led us to examine a synthetic variant that should allow easy connection with other subunits of the projected convergent synthesis of this antibiotic.