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Beilstein J. Org. Chem. 2022, 18, 653–659, doi:10.3762/bjoc.18.66
Graphical Abstract
Figure 1: Structure of lumateperone.
Scheme 1: First synthetic route leading to lumateperone (1).
Scheme 2: Alternate synthesis of lumateperone.
Scheme 3: Alternate synthetic approaches leading to racemic lumateperone ((±)-1)).
Scheme 4: Planned new synthesis of key intermediate (±)-9a.
Scheme 5: New synthesis of key intermediate (±)-9a.
Scheme 6: Trifluoroacetylation of tetrahydroquinoxaline (37).
Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136
Scheme 1: Rearrangement of methylenedioxy-substituted aminoaldehyde 1a to regioisomer 2a and formation of the...
Scheme 2: Synthesis of 1-arylisoindoles 6 and formation of dimers 5.
Scheme 3: Rearrangement of aminoaldehydes 1 to regioisomers 2 and formation of dimer-like products 3 and 8.
Figure 1: X-ray structures of compounds 3b (left) and 8b (right).
Scheme 4: Proposed mechanism of the isomerization of aldehydes 1 via isoindoles 4.
Scheme 5: Proposed mechanism of the formation of dimer-like products 3a,b.
Scheme 6: Proposed mechanism for the formation of dimer-like products 8a,b.
Scheme 7: Dimerization of indole under acidic conditions.
Figure 2: Gibbs free energy diagram for the 1→2 rearrangement.
Scheme 8: Reaction of o-(pivaloylaminomethyl)benzaldehyde (1e) to give dimer-like products 23a and 23b.
Figure 3: X-ray structures of compounds 23a (left) and 23b (right).
Figure 4: Structures of the minimal energy conformer of stereoisomer 23a and those of two minimal energy conf...