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53. Bioinspired Synthesis of Pentacyclic Onocerane Triterpenoids

F. Bartels, Y. J. Hong, D. Ueda, M. Weber, T. Sato, D. J. Tantillo, M. Christmann

The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.

Title
53. Bioinspired Synthesis of Pentacyclic Onocerane Triterpenoids
Author
F. Bartels, Y. J. Hong, D. Ueda, M. Weber, T. Sato, D. J. Tantillo, M. Christmann
Identifier
DOI: 10.1039/C7SC03903D
Citation
Chem. Sci. 2017, 8, 8285–8290.