Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

Clawson, Ronald W.; Dacko, Christopher A.; Deavers, Robert E.; Akhmedov, Novruz G.; Söderberg, Björn C.G.

doi:10.1016/j.tet.2009.08.055

Cited by 21 publications

(8 citation statements)

References 28 publications

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“…The synthesis of 2‐octadecyl,3‐methoxyindole by the same catalytic system unexpectedly failed, but use of the Pd(OAc) 2 /Phen combination allowed the reaction to go to completion . Attempts to transform the methoxy group into the hydroxy one, failed (Scheme ) …”

Section: Synthesis Of N‐heterocycles By Intra‐molecular Cyclization Rmentioning

confidence: 99%

“…In the same work, the cyclization of a nitrostyrene bearing a triethylsilyl group in the α position was attempted. The indole was obtained in good yields, but the silyl group was lost in the process (Scheme ) . Such a loss of a functional group is unprecedented in this chemistry, but there is no other data in the literature to confirm if it constitutes a general reactivity.…”

Section: Synthesis Of N‐heterocycles By Intra‐molecular Cyclization Rmentioning

confidence: 99%

“…[117] The synthesis of 2-octadecyl,3-methoxyindole by the same catalytic system unexpectedly failed, but use of the Pd(OAc) 2 / Phen combination allowed the reaction to go to completion. [118] Attempts to transform the methoxy group into the hydroxy one, failed (Scheme 15). [118] In the same work, the cyclization of a nitrostyrene bearing a triethylsilyl group in the α position was attempted.…”

Section: Synthesis Of Indolesmentioning

confidence: 99%

“…[118] Attempts to transform the methoxy group into the hydroxy one, failed (Scheme 15). [118] In the same work, the cyclization of a nitrostyrene bearing a triethylsilyl group in the α position was attempted. The indole was obtained in good yields, but the silyl group was lost in the process (Scheme 16).…”

Section: Synthesis Of Indolesmentioning

confidence: 99%

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Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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Nitroarenes are the entry point for the production of most nitrogen‐containing aromatic compounds. Thus, any transformation that leads directly from them to the final product allows saving one or more synthetic steps. This review deals with homogeneously catalyzed reactions leading to the formation of N‐heterocyclic compounds from nitroarenes or nitroalkenes in one pot. Reactions that lead to the intermediate formation of amines are not considered. Carbon monoxide is the most often employed reductant because it allows selective reactions, is cheap, and only produces CO2 as stoichiometric byproduct. However, the difficulty in handling pressurized CO has stimulated in recent years the development of CO‐surrogates, that is molecules able to liberate CO during the reaction. The use of phosphines and diols has also been developed in conjunction with molybdenum catalysts. The review focusses in more detail on the literature in the period 2006–2018, but reference to earlier work is made when necessary to put recent results in a more general context.

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Section: Synthesis Of N‐heterocycles By Intra‐molecular Cyclization Rmentioning

confidence: 99%

Section: Synthesis Of N‐heterocycles By Intra‐molecular Cyclization Rmentioning

confidence: 99%

Section: Synthesis Of Indolesmentioning

confidence: 99%

Section: Synthesis Of Indolesmentioning

confidence: 99%

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Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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“…Söderberg's method has been successfully applied to the synthesis of a number of indole analogs including tryptophan derivatives, 14 bicyclic heteroaromatics, 15 carbazole alkaloids, 16 mushroom metabolites, 17 and various natural products. [18][19][20][21][22][23][24][25] Through a detailed optimization study of the reaction conditions, it was observed that the Pd(dba)2-dppp-1,10-phenanthroline system using DMF as solvent at 120 °C under 6 atm of carbon monoxide (Scheme 3) was highly applicable to late stage indolization during many natural products syntheses.…”

Section: Scheme 2: Watanabe and Söderberg Reductive Heterocyclizationmentioning

confidence: 99%

Syntheses of azepinoindole alkaloids cimitrypazepine, fargesine and hyrtioreticulins C & D

Ghimire¹

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Syntheses of azepinoindole alkaloids cimitrypazepine, fargesine and hyrtioreticulins C & D Ganesh Ghimire The Watanabe-Cenini-Söderberg reductive N-heterocyclization has emerged as a powerful tool for the synthesis of a variety of functionalized indoles. Söderberg's elaboration of this methodology has been utilized as a late-stage cyclization protocol for the synthesis of azepinoindole alkaloids, a class of natural products characterized by an azepane skeleton fused with an indole ring. Short syntheses of the naturally occurring azepino[5,4,3-cd]indole alkaloids, cimitrypazepine, fargesine, and the diastereomeric hyrtioreticulins C & D have been completed starting from commercially available tetra-substituted benzene derivatives. The key azepinoindole core in each case was assembled via an intramolecular Mizoroki-Heck reaction followed by a Watanabe-Cenini-Söderberg reductive N-heterocyclization. Synthesis of aurantioclavine using a similar strategy is currently underway.

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Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Söderberg

Berkowitz

2022

Organic Reactions

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This chapter presents a comprehensive review of reductive cyclizations of 2‐nitro‐ and β‐nitrostyrenes, 2‐nitrobiphenyls, and 1‐nitro‐1,3‐dienes to furnish indoles, carbazoles, and pyrroles, respectively, as well as heteroatom analogs thereof. Two variations of the reductive cyclization are discussed: the Cadogan–Sundberg reaction, which is mediated by ternary phosphorus compounds, and the Watanabe–Cenini–Söderberg reaction, which employs a palladium catalyst in the presence of carbon monoxide. A few closely related reductive cyclizations are also presented, as are comparisons with other cyclizations that form the nitrogen–carbon bond of indoles and derivatives.

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Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

Cited by 21 publications

References 28 publications

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Syntheses of azepinoindole alkaloids cimitrypazepine, fargesine and hyrtioreticulins C & D

Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

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