Construction of sulfur-containing moieties in the total synthesis of natural products

Wang, Nengzhong; Saidhareddy, Puli; Jiang, Xuefeng

doi:10.1039/c8np00093j

Cited by 502 publications

(248 citation statements)

References 186 publications

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“…We first investigated decarboxylative/ deaminative thiolation reactions. Organosulfur molecules are important motifs found in organic synthesis and functional molecules 56,57 . The most straightforward construction of C (sp 3 )-S bond is the nucleophilic substitution reaction of an alkyl halide with a mercaptan.…”

Section: Resultsmentioning

confidence: 99%

Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

et al. 2020

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Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

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Section: Resultsmentioning

confidence: 99%

Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

et al. 2020

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“…It is known that the functions of proteins can be switched via the cleavage or formation of disulfides is known [10,11]. Disulfides are found in some small molecules that are biologically active natural products [12].…”

Section: Structure and Reactivity Of Organic Disulfidesmentioning

confidence: 99%

Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur

Arisawa

Yamaguchi

2020

Molecules

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Organosulfur compounds are widely used for the manufacture of drugs and materials, and their synthesis in general conventionally employs nucleophilic substitution reactions of thiolate anions formed from thiols and bases. To synthesize advanced functional organosulfur compounds, development of novel synthetic methods is an important task. We have been studying the synthesis of organosulfur compounds by transition-metal catalysis using disulfides and sulfur, which are easier to handle and less odiferous than thiols. In this article, we describe our development that rhodium complexes efficiently catalyze the cleavage of S-S bonds and transfer organothio groups to organic compounds, which provide diverse organosulfur compounds. The synthesis does not require use of bases or organometallic reagents; furthermore, it is reversible, involving chemical equilibria and interconversion reactions.

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“…2 Furthermore, these effects were found in anti-cancer natural products 9 and peptides 10 for the expression of cytoxicity and receptor-selectivity as well. 11,12 Therefore, efficient construction of steric and stereoscopic disuldes for molecule cross-linkage is urgently demanded. Although substitution of tertiary thiols with preactivated S-partners is conventionally employed for the synthesis of steric disuldes (Scheme 1b), 13 adjacent variation of hindrance, stereocenter construction and molecule-crosslinkage remain underdeveloped.…”

Section: Introductionmentioning

confidence: 99%

Steric and stereoscopic disulfide construction for cross-linkage via N-dithiophthalimides

et al. 2020

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Construction of sulfur-containing moieties in the total synthesis of natural products

Abstract: This review surveys the total syntheses of sulfur-containing natural products where sulfur atoms are introduced with different sulfurization agents to construct related sulfur-containing moieties.

Cited by 502 publications

References 186 publications

Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur

Steric and stereoscopic disulfide construction for cross-linkage via N-dithiophthalimides

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