Synthesis of (±)-demethoxypauciflorine B and (±)-pauciflorine B from (±)-11,12-demethoxylahadinine B and (±)-lahadinine B, respectively via a peroxycarbanolamine fragmentation reaction

Magnus, Philip; Hobson, L.; Westlund, Neil; Lynch, Vincent M.

doi:10.1016/s0040-4039(00)02218-8

Cited by 18 publications

(13 citation statements)

References 14 publications

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“…171,172 An example of Magnus’ use of this reaction en route to lahadinine B ( 40 ) is shown in Figure 37. The reaction proceeds in 83% yield to convert 38 to 39 in a completely diastereo- and regioselective manner.…”

Section: C-o Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

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Cofactor-mimetic aerobic oxidation has conceptually merged with catalysis of syngas reactions to form a wide range of Markovnikov-selective olefin radical hydrofunctionalizations. We cover the development of the field and review contributions to reaction invention, mechanism and application to complex molecule synthesis. We also provide a mechanistic framework for understanding this compendium of radical reactions.

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Section: C-o Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

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“…190,191 The transannular cyclization of eleven-membered precursor 665 set the stage for the key Diels-Alder reaction. The Diels-Alder adduct was obtained on treatment of the cyanide 666 with acryloyl chloride.…”

Section: Application Of Bridged Lactams In Total Synthesismentioning

confidence: 99%

“…Magnus utilized a similar concept based on the peroxyaminal fragmentation of the intermediate 672 in the total synthesis of pauciflorine B (Scheme 184b). 190,191 …”

Section: Application Of Bridged Lactams In Total Synthesismentioning

confidence: 99%

“…Kopsijasminilam ( 671 ) and pauciflorine B ( 674 ) (Scheme 187) have been mentioned in the previous section in the context of their synthesis (see Section 8.7); 190–192 two other Kopsia alkaloids, deoxykopsijasminilam ( 702 ) and pauciflorine A ( 703 ) 190–192 share their unprecedented skeleton (Scheme 187). The Amaryllidaceae alkaloids containing bridged amide bonds, cripowellins A and B ( 598–599 ) (Scheme 188), 465 have been already discussed in this review (see Section 8.3).…”

Section: Application Of Bridged Lactams In Total Synthesismentioning

confidence: 99%

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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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“…The new biosynthetic hypothesis starts with the hydrolysis of kopsijasminilam-type precursors to pyrroline-containing carboxylic acids 28 (Scheme ). The close proximity between C20 and amide N atom in known kopsijasminilam-type structures suggests that lactam hydrolysis might involve N -acyl ammonium cations 29 as key intermediates. , Indeed, the DFT optimization of kopsijasminilam-type structures with planar amide and the carbocation at C20 led to more stable cations 29 that have short C20–N distances (ca. 1.62 Å), nonplanar nitrogen atoms, and elongated amide C21–N bonds (ca.…”

Section: Resultsmentioning

confidence: 99%

Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

et al. 2018

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The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.

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Synthesis of (±)-demethoxypauciflorine B and (±)-pauciflorine B from (±)-11,12-demethoxylahadinine B and (±)-lahadinine B, respectively via a peroxycarbanolamine fragmentation reaction

Cited by 18 publications

References 14 publications

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Chemistry of Bridged Lactams and Related Heterocycles

Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

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