Beilstein J. Org. Chem.2021,17, 2729–2764, doi:10.3762/bjoc.17.185
., fredericamycin A and acutumine [99]), SPINOL-based ligands and catalysts [100], and organometallic complexes with important applications. The use of chiral catalysts for spirocyclization reactions brings asymmetry at the site of the spirocyclic center while tolerating different electronic and steric functional
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Graphical Abstract
Figure 1:
Representative examples of axially chiral biaryls, heterobiaryls, spiranes and allenes as ligands a...
Beilstein J. Org. Chem.2011,7, 1475–1485, doi:10.3762/bjoc.7.171
activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits.
Keywords: alkaloids; directed aromatic functionalization; fredericamycin; heterocyclic compounds; lithiation
specific synthetic endeavors in our group. Herein, we illustrate the application of such techniques to three representative problems that we have addressed over the years: The syntheses of fredericamycin A, nothapodytine B, and topopyrones B and D.
Fredericamycin A
This initial portion of the present
review recounts the first project that the senior author of this paper launched as an independent academic in 1984. A structurally novel natural product by the name of fredericamycin A (1, Scheme 1) had been discovered only two years prior and determined to be strongly cytotoxic [1][2][3][4][5]: A
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Graphical Abstract
Scheme 1:
Structure and retrosynthetic analysis of fredericamycin A.