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Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222
Graphical Abstract
Figure 1: Marine pyridoacridine alkaloids amphimedine (1), ascididemin (2), kuanoniamine A (3), styelsamine D...
Figure 2: A–C): Published methods for the synthesis of 4,5-disubstituted benzo[c][2,7]naphthyridines; D) New ...
Scheme 1: Regioselective metalation of 4-bromobenzo[c][2,7]naphthyridine (9d) and subsequent conversion into ...
Scheme 2: Outcome of a D2O quenching experiment after metalation of 4-bromobenzo[c][2,7]naphthyridine (9d).
Scheme 3: Synthesis of 5-substituted 4-bromobenzo[c][2,7]naphthyridines via regioselective metalation of 9d u...
Scheme 4: Attempted synthesis of kuanoniamine A (3).
Scheme 5: Synthesis of pyrido[4,3,2-mn]acridone 22 starting from 20a via bromine–magnesium exchange reaction ...
Beilstein J. Org. Chem. 2018, 14, 130–134, doi:10.3762/bjoc.14.8
Figure 1: Previously published total syntheses of alkaloid 1 [11,12].
Scheme 1: Total synthesis of alkaloid 1 via direct ring metalation and methylation.
Scheme 2: Total synthesis of alkaloid 1 via the aminomethyl intermediate 5 and selectivity’s found in debenzy...
Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156
Figure 1: Prominent oxoaporphine and oxoisoaporphine alkaloids: liriodenine (1), menisporphine (2), dauriporp...
Scheme 1: Previously reported [7,17] and new approach to oxoisoaporphine alkaloids.
Scheme 2: Synthesis of iodinated isoquinolines 8a–c from alkoxy-substituted isoquinolines 7a–c.
Scheme 3: Synthesis of methyl 2-(isoquinolin-1-yl)benzoates 10a–c from 1-iodoisoquinolines 8a–c.
Scheme 4: Synthesis of the alkaloids 6-O-demethylmenisporphine (4), dauriporphinoline (5), and bianfugecine (6...
Scheme 5: Attempted synthesis of bianfugecine (6) via directed remote metalation and subsequent trapping of t...
Scheme 6: Outcome of a D2O quenching experiment after metalation of amide 12.
Scheme 7: Synthesis of 1-arylnaphthalene analogues 15 and 16.
Scheme 8: Outcome of a D2O quenching experiment after metalation of amide 16 with LDA.
Scheme 9: Synthesis of the alkaloids menisporphine (2) and dauriporphine (3) by O-methylation of the alkaloid...