Synthesis and crystal structure analysis of substituted bicyclo[3.3.1]nonanones

Abstract

A set of novel bicyclo[3.3.1]nonanones, namely, 4-methoxybicyclo[3.3.1]non-3-ene-2,9-dione, C10H12O3 (1), 4,9,9-trimethoxybicyclo[3.3.1]non-3-en-2-ol, C12H20O4 (2), 4-methoxy-6-methyl-1-(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione, C22H32O3 (3) and 4-(tert-butyl)-4-hydroxy-2-methoxy-8-methyl-7-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-2-en-9-one, C26H42O3 (4), were synthesized and structurally elucidated by NMR, HRMS and X-ray crystallography.

Keywords

• polycyclic
• polyprenylated acylphloroglucinol
• ppaps
• bridgehead substitution
• carbocycles
• crystal structure