Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols

In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.

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Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem

Synthesis ◽

10.1055/s-0040-1706103 ◽

2020 ◽

Author(s):

Narendra R. Chaubey ◽

Anant R. Kapdi ◽

Biswanath Maity

Keyword(s):

Total Synthesis ◽

Room Temperature ◽

Drug Molecule ◽

Bond Functionalization ◽

First Report ◽

Mild Conditions ◽

The Past ◽

Hypnotic Drug ◽

Free Environment

AbstractOrganophotocatalytic C–H bond functionalization has attracted a lot of attention in the past several years due to the possibility of catalyzing reactions in a metal- and peroxide-free environment. Continuing on these lines, an organophotoredox-catalyzed C–H functionalization of imidazo[1,2-a]pyridines and related heterocycles with bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative-hypnotic drug molecule.

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Adamantanethione and its reduction to 2-adamantanethiol

Canadian Journal of Chemistry ◽

10.1139/v69-619 ◽

1969 ◽

Vol 47 (19) ◽

pp. 3715-3716 ◽

Cited By ~ 15

Author(s):

J. W. Greidanus ◽

W. J. Schwalm

Keyword(s):

Sodium Borohydride ◽

Phosphorus Pentasulfide ◽

Indirect Route

Reaction of adamantanone with phosphorus pentasulfide affords the corresponding thioketone. This new, comparatively very stable alicyclic thione was also obtained by an indirect route from 2-ethoxy-2-adamantanethiol. Reduction of the thioketone with sodium borohydride yields 2-adamantanethiol.

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Short and Diastereoselective Total Synthesis of the Polyhydroxylated Pyrrolidine LAB-1: A Potent α-Glycosidase Inhibitor

Synthesis ◽

10.1055/s-0036-1590799 ◽

2017 ◽

Vol 49 (21) ◽

pp. 4869-4875 ◽

Cited By ~ 3

Author(s):

Fernando Coelho ◽

Erica da Silva ◽

Nathália Yamakawa ◽

Alcindo Dos Santos

Keyword(s):

Total Synthesis ◽

Optically Active ◽

Biologically Active ◽

First Report ◽

Glycosidase Inhibitor

We described herein a total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol [(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol, LAB-1], a polyhydroxylated pyrrolidine, which has been demonstrated to be a selective and potent α-glycosidase inhibitor. The main features of our approach are its shortness, efficiency, and simplicity. The total synthesis was accomplished in 6 steps with an overall yield of 12%, starting from a chiral optically active Morita–Baylis–Hillman (MBH) adduct prepared (without epimerization), from Garner’s aldehyde. As far as we know, this is the first report describing the total synthesis of this biologically active pyrrolidine by exploring the synthetic versatility of a MBH adduct.

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A fossil Aspergillus from Eocene Dominican amber

Journal of Paleontology ◽

10.1017/s0022336000058996 ◽

1988 ◽

Vol 62 (01) ◽

pp. 141-143 ◽

Cited By ~ 15

Author(s):

Gerard M. Thomas ◽

George O. Poinar

Keyword(s):

Dominican Republic ◽

Fossil Species ◽

First Report ◽

Dominican Amber ◽

Eocene Amber

A sporulating Aspergillus is described from a piece of Eocene amber originating from the Dominican Republic. The Aspergillus most closely resembles a form of the white spored phase of Aspergillus janus Raper and Thom. This is the first report of a fossil species of Aspergillus.

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