Synthesis of the core of apicularen A by transannular conjugate addition

✍ Scribed by Ferdows Hilli; Jonathan M. White; Mark A. Rizzacasa

• Book ID: 104252265
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 311 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02069-5

✦ Synopsis

The synthesis of the core of the myxobacteria metabolite apicularen A by a novel transannular 1,4-addition is described. The key step involved acid mediated transannular conjugate addition of the C13 hydroxyl into the a,b-unsaturated ketone in macrolactone 18 to provide the trans-pyranone 19 and the cis-isomer 20 in a ratio of 9:1, respectively.