2022
DOI: 10.1021/jacs.2c06015
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Total Synthesis of Bipolamine I

Abstract: Indolizidine alkaloids have been the target of chemical and biological studies for decades, most recently highlighted by the isolation of the curvulamine and bipolamine polypyrrole-containing subclass. Herein we report a stereoselective 15-step synthesis of bipolamine I, a distinct member of the broader family, and through this work develop an intermediate that will serve to access other polypyrrole natural products and key analogues going forward.

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Cited by 4 publications
(1 citation statement)
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“…While the initial stages of biosynthesis have been explored for simple C 10 members (e.g 2 and 3 ), [4] the enzymology underpinning the construction of complex 20‐carbon members (see 1 , 4 – 10 ) remains mysterious. In 2020 we reported the first and only synthetic route to 1 , [5] and very recently, Qiu and Pierce described an elegant total synthesis of bipolamine I ( 10 ) [6] . Herein we report total syntheses of bipolamines D, E, G, and I from a common bispyrrole core now accessible in gram quantities.…”
Section: Figurementioning
confidence: 95%
“…While the initial stages of biosynthesis have been explored for simple C 10 members (e.g 2 and 3 ), [4] the enzymology underpinning the construction of complex 20‐carbon members (see 1 , 4 – 10 ) remains mysterious. In 2020 we reported the first and only synthetic route to 1 , [5] and very recently, Qiu and Pierce described an elegant total synthesis of bipolamine I ( 10 ) [6] . Herein we report total syntheses of bipolamines D, E, G, and I from a common bispyrrole core now accessible in gram quantities.…”
Section: Figurementioning
confidence: 95%