Büchi G,
*,
Chu P.-S.
Massachusetts Institute of Technology, Cambridge, USA
Synthesis of Gymnomitrol.
J. Am. Chem. Soc. 1979;
101: 6767-6768
DOI:
10.1021/ja00516a056
Key words
(±)-gymnomitrol - Dakin oxidation - [4+2] cycloaddition - Birch reduction - Wittig reaction
Significance
In 1979, Büchi and Chu reported the total synthesis of (±)-gymnomitrol, a sesquiterpenoid isolated from the liverwort Gymnomitrion obtusum (Lindb) Pears. Structural features of the natural product include a tricyclo[5.3.1.02,6]undecane skeleton containing five contiguous stereocenters and an exocyclic methylene.
Comment
Aldehyde A was converted into alcohol C by Dakin oxidation. Dearomatization afforded ketal D which underwent [4+2] cycloaddition with cyclopentene E to furnish the carbon skeleton of the natural product. Further elaboration yielded (±)-gymnomitrol.
