Asymmetric Synthesis of 2‐Heteroaryl Cyclic Amines: Total Synthesis of (–)‐Anabasine

Abstract

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Organophosphates as Versatile Substrates in Organic Synthesis

“…In contrast, the published preparation of (–)-anabasine ( 21 – 5 ) took advantage of the palladium-catalyzed Suzuki–Miyaura borylation. This process was applied to crudely isolated phosphate 21 – 2 in the presence of barium hydroxide ( Scheme 21 ) [ 106 ]. The prepared pinacol boronic acid ester 21 – 3 was treated with 3-bromopyridine to give alkene 21 – 4 with a 56% isolated yield.…”

Efficient Cross‐Coupling of Dioxazaborocanes with α‐Phosphate Enamides

“…To the best of our knowledge, this reactivity is surprisingly unprecedented and would constitute a powerful and selective strategy to generate differently substituted aza‐heterocycles. As an extension of our interest in enamide functionalization using metal catalysis,3d,5b,13 we report herein an efficient cross‐coupling of α‐phosphate enamides (i.e. ene‐carbamates) and dioxazaborocanes (DABO boronates) (Figure 1).…”

Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

“…Azepanes display activity as glycosidase inhibitors, − norepinephrine and dopamine transporters or protein kinase C inhibitors, and are promising candidates for the treatment of viral infections, diabetes or cancer. ,, Natural products and medicinal agents incorporating the azepane ring (Scheme a) include balanol, zilpaterol, azelastine, capuramycin , and Stemona alkaloids . Azepane 1 is a potential therapeutic agent against cancer, and 2 is an inhibitor of NET/DAT . The benzazepine core is also present in fenoldopam and lorcaserin 3…”

“…7a,11a,b Natural products and medicinal agents incorporating the azepane ring (Scheme 1a) include balanol, 9 zilpaterol, 9 azelastine, 12 capuramycin 6,13 and Stemona alkaloids. 14 Azepane 1 is a potential therapeutic agent against cancer, 15 and 2 is an inhibitor of NET/DAT. 8 The benzazepine core is also present in fenoldopam 16a and lorcaserin 3.…”