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1 article(s) from Porto, Ricardo S

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

Dimas J. P. Lima,
Antonio E. G. Santana,
Michael A. Birkett and
Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

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Graphical Abstract

Figure 1: Homotropane (azabicyclononane) systems.

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Figure 2: Alkaloids (−)-adaline (1), (+)-euphococcinine (2) and (+)-N-methyleuphococcinine (3).

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Scheme 1: Synthetic strategies before 1995.

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Scheme 2: Synthesis (±)-adaline (1) and (±)-euphococcinine (2). Reagents and conditions: i) 1. dihydropyran, ...

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Scheme 3: Synthesis (+)-euphococcinine (2). Reagents and conditions: i) H₂O₂, SeO₂ (cat), acetone, rt, 88%; i...

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Scheme 4: Synthesis (+)-euphococcinine (2). Reagents and conditions: i) 2,4-bis(4-phenoxyphenyl)-1,3-dithia-2...

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Scheme 5: Synthesis of (±)-euphococcinine precursor (±)-42. Reagents and conditions: i) Bu₃SnH, AIBN, toluene...

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Scheme 6: Synthesis of (−)-adaline (1). Reagents and conditions: i) LiH₂NBH₃, THF, 40 °C, 88%; ii) TPAP, NMO,...

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Scheme 7: Synthesis of (−)-adaline (1) and (−)-euphococcinine (2). Reagents and conditions: i) 1. BuLi, t-BuO...

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Scheme 8: Synthesis of (−)-adaline (1). Reagents and conditions: i) Ref. [52]; ii) Et₃N, TBDMSOTf, CH₂Cl₂, 0 °C t...

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Scheme 9: Synthesis of (+)-euphococcinine (2). Reagents and conditions: i) 1. Cp₂ZrCl₂,AlMe₃, CH₂Cl₂; 2. p-me...

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Scheme 10: Synthesis of (−)-adaline 1. Reagents and conditions: i) 1. CuBr^.DMS, Et₂O/DMS, -42 ºC; 2. 1-heptyne...

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Scheme 11: Synthesis of (−)-euphococcinine (2) and (−)-adaline (1). Reagents and conditions: i) 102, KHMDS, Et₂...

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Scheme 12: Synthesis of N-methyleuphococcinine 3. Reagents and conditions: i) 108 (1.5 equiv), 3,5-di-F-C₆H₃B(...

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Review

Published 05 Jan 2021

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