ChemInform Abstract: THE TOTAL SYNTHESIS OF RACEMIC NAPELLINE

Wiesner, K.; Ho, Pak-Tsun; Tsai, Connie S. J.; Lam, Yu‐hong

doi:10.1002/chin.197437419

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2019

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“…atropurpureum in 2009. 13 While syntheses of the members from most C 20diterpenoid alkaloid types and structurally related diterpenes have been accomplished in the synthetic community, [3][4][5][6][7][8][9]14 the total synthesis of an arcutine-type alkaloid remains unsolved. Because of our continuous interest in the synthesis of complex diterpenoids and related alkaloids, 3c,e,4j,14c here we report the first total synthesis of arcutinine (2) in both racemic and asymmetric forms.…”

Section: ■ Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of (−)-Arcutinine

et al. 2019

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The first total synthesis of an arcutine-type C20-diterpenoid alkaloid arcutinine has been achieved in both racemic and asymmetric forms. Construction of the C4 quaternary center and the pyrrolidine E ring in an early stage proved to be important for achieving the successful synthesis of the target alkaloid. Strategically, an asymmetric conjugate addition/aldol cascade and a decarboxylative allylation reaction allowed the establishment of the vicinal all-carbon quaternary stereocenters at C4 and C5. Furthermore, a sequence consisting of an intramolecular aza-Wacker cyclization, an oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade, and a ketyl-olefin cyclization enabled the assembly of the core structure and led to the total synthesis of arcutinine.

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Section: ■ Introductionmentioning

confidence: 99%