2016 journal article
Studies toward the Synthesis of Lepadiformine A
JOURNAL OF ORGANIC CHEMISTRY, 81(21), 10433–10443.
MeSH headings : Alkaloids / chemical synthesis; Alkaloids / chemistry; Animals; Carbon-13 Magnetic Resonance Spectroscopy; Cyclization; Molecular Structure; Proton Magnetic Resonance Spectroscopy; Stereoisomerism; Urochordata / chemistry
TL;DR:
An original approach to access a tricyclic framework of the lepadiformine-type alkaloids using a Grignard/N-acylpyridinium salt reaction to establish the desired absolute stereochemistry at the C2 position of the target alkaloid.
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(Web of Science)
Source: Web Of Science
Added: August 6, 2018
Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction of a 4-methoxytetrahydroquinoline is the key carbon-carbon bond-forming step that was used to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. The synthesis features an allylation reaction with an N-acyliminium ion to set the C10 quaternary stereocenter, a mild dissolving-metal cleavage of hindered phenyl carbamates, and an aminoiodocyclization to form the pyrrolidine ring. While this route does not provide the correct C10 stereochemistry, it showcases an efficient method to build analogues with the ring system of this class of alkaloids in 11 steps overall.