A new synthesis of a stemmadenine model

Wu, Anthony; Snieckus, Victor

doi:10.1016/s0040-4039(00)75293-2

Cited by 39 publications

(10 citation statements)

References 17 publications

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“…Tandem lactam/olefin reduction and oxidative cyclization using PtO 2 /O 2 transformed the lactam 638 into the natural product. Similar Witkop photocyclizations to give bridged lactams in the synthesis of Strychnos alkaloids have been reported independently by Snieckus 177 and Ishikura. 178 …”

Section: Application Of Bridged Lactams In Total Synthesissupporting

confidence: 72%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Application Of Bridged Lactams In Total Synthesissupporting

confidence: 72%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…Applications of the original Madelung method are tabulated in Table 1 [11][12][13][14][15][16][18][19][20][21][22][23][24][25]. As was found earlier, Augustine observed that potassium tert-butoxide is superior to sodium methoxide, sodamide, lithium amide, and n-butyllithium (Entries 4-6) [13].…”

mentioning

confidence: 73%

Madelung Indole Synthesis

Gribble

2016

Indole Ring Synthesis

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“…Die Einführung von zusätzlichen Substituenten am Piperidinring führte zu drastisch verlängerten Reaktionszeiten und einem Abfall der Ausbeute auf 15 % 11. Reduktion der Doppelbindung zum Ethylrest und nachfolgende Bestrahlung führten zu Ausbeuten um 20 % für das cyclisierte Produkt 12. Es wird angenommen, dass die Ethylidengruppe in 26 eine Vorzugskonformation einnimmt, bei der die beiden Reaktionszentren nahe zueinander stehen und daher höhere Ausbeuten zustande kommen.…”

Section: Photocyclisierung Von 2‐substituierten Indolenunclassified

Phenylene‐bridged β‐Ketoiminate Dilanthanide Aryloxides: Synthesis, Structure, and Catalytic Activity for Addition of Amines to Carbodiimides

Hong

Zheng

Xue

et al. 2015

Zeitschrift anorg allge chemie

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The synthesis and reactivity of a series of bimetallic lanthanide aryloxides stabilized by a p‐phenylene‐bridged bis(β‐ketoiminate) ligand is presented. The reaction of 1,4‐diaminobenzene with acetylacetone in a 1:2.5 molar ratio in absolute ethanol gave the compound 1,4‐bis(4‐imino‐2‐pentanone)benzene (1) (LH2) in high yield. Compound 1 reacted with (ArO)3Ln(THF)2 (ArO = 2,6‐tBu2‐4‐MeC6H2O, THF = tetrahydrofuran) in a 1:2 molar ratio in THF, after workup, to give the corresponding dilanthanide aryloxides L[Ln(OAr)2(THF)]2 [Ln = Yb (2), Y (3), Sm (4), Nd (5), La (6)] in high isolated yields. Compound 1 and complexes 2–6 were fully characterized, including X‐ray crystal structure analyses for complexes 2, 3, 5, and 6. Complexes 2–6 can be used as efficient pre‐catalysts for catalytic addition of amines to carbodiimides, and the ionic radii of the central metal atoms have a significant effect on the catalytic activity with the increasing sequence of La (6) < Nd (5) ≈ Sm (4) < Y (3) ≈ Yb (2). The catalytic addition reaction with 2 showed a good scope of substrates including primary and secondary amines.

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A new synthesis of a stemmadenine model

Cited by 39 publications

References 17 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Madelung Indole Synthesis

Phenylene‐bridged β‐Ketoiminate Dilanthanide Aryloxides: Synthesis, Structure, and Catalytic Activity for Addition of Amines to Carbodiimides

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