Tetrahedron letters

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

ME Jung, JM MacDougall

Index: Jung, Michael E.; MacDougall, James M. Tetrahedron Letters, 1999 , vol. 40, # 35 p. 6339 - 6342

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Citation Number: 17

Abstract

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.