Synthesis of Cycle B Functionalized Derivatives of (+)-Larixol

Abstract

The main purpose of this research was the synthesis of highly functionalized derivatives of (+)-larixol by combination of classical and nonconventional method, like dye-sensitized photooxidation with preservation of outside chain. As a result, a series of four new cycle B derivatives of (+)-larixol were obtained, including products of photooxidative dehydrogenation and [2+4] cycloaddition of singlet oxygen, compounds 7 and 8, respectively. The structure of all synthesized compounds was fully confirmed by spectral method (IR, 1H and 13C NMR) and for compound 8 containing endoperoxide functional group, additionally by single crystal X-ray diffraction analysis.

Keywords

• (+)-larixol
• enolacetylation
• dye-sensitized photooxidation
• reduction
• x-ray analysis