Bioinspired synthesis of pentacyclic onocerane triterpenoids. Issue 12 (23rd October 2017)

• Record Type: Journal Article
• Authors: Bartels, Florian; Hong, Young J.; Ueda, Daijiro; Weber, Manuela; Sato, Tsutomu; Tantillo, Dean J.; Christmann, Mathias
• Is Part Of: Chemical science. Volume 8:Issue 12(2017)
• Page Start: 8285
• Page End: 8290
• Publication Date: 2017-10-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc03903d
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The first chemical synthesis of pentacyclic onocerane triterpenoids (+)-cupacinoxepin and (+)-onoceranoxide is described. Abstract : 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.