First enantioselective total synthesis of the endogenous natriuretic agent LLU-α

Article abstract of DOI:10.1016/S0040-4039(99)01204-6

The endogenous natriuretic agent LLU-α, 1, has been synthesized from geraniol 4 in 13 steps and 18% overall yield. The two key steps are a Gassman-Sato process to give the phenol 8 and cyclization of the triol 10 with acid to give the chroman 12 with retention of configuration at the tertiary alcohol center. Final oxidation gave 1.