Synthesis of (−)-Neothiobinupharidine

Jansen, Daniel J.; Shenvi, Ryan A.

doi:10.1021/ja310778t

Cited by 58 publications

(53 citation statements)

References 36 publications

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“…Nevertheless, the level of simplification provided by the dimerization Tf. prompted the authors of this review to explore the corresponding transformation in the laboratory [47]. …”

Section: Transform-based Strategies: the Power Of The ‘Key Step′mentioning

confidence: 99%

Synthesis of Medicinally Relevant Terpenes: Reducing the Cost and Time of Drug Discovery

Jansen

Shenvi

2014

Future Med. Chem.

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Terpenoids constitute a significant fraction of molecules produced by living organisms that have found use in medicine and other industries. Problems associated with their procurement and adaptation for human use can be solved using chemical synthesis, which is an increasingly economical option in the modern era of chemistry. This article documents, by way of individual case studies, strategies for reducing the time and cost of terpene synthesis for drug discovery. A major trend evident in recent syntheses is that complex terpenes are increasingly realistic starting points for both medicinal chemistry campaigns and large-scale syntheses, at least in the context of the academic laboratory, and this trend will likely penetrate the commercial sector in the near future.

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“…Nevertheless, the level of simplification provided by the dimerization Tf. prompted the authors of this review to explore the corresponding transformation in the laboratory [47]. …”

Section: Transform-based Strategies: the Power Of The ‘Key Step′mentioning

confidence: 99%

Synthesis of Medicinally Relevant Terpenes: Reducing the Cost and Time of Drug Discovery

Jansen

Shenvi

2014

Future Med. Chem.

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“…One example is the thiaspirane nuphar dimers, where Shenvi and co-workers were able to demonstrate a biomimetic approach through a sulfurizing dimerization of an enamine intermediate. [12] …”

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confidence: 99%

Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Legako

et al. 2016

Chemistry A European J

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Dibohemamines A–C (5–7), three novel dimeric bohemamine analogs dimerized through a methylene group, were isolated from a marine-derived Streptomyces spinoverrucosus. The structures determined by spectroscopic analysis were confirmed through the semi-synthetic derivatization of monomeric bohemamines and formaldehyde. These reactions, which could occur under mild conditions, together with the detection of formaldehyde in the culture, revealed that this dimerization is a non-enzymatic process. In addition to the unique dimerization of the dibohemamines, dibohemamines B and C were found to have nM cytotoxicity against the non-small cell lung cancer cell line A549. In view of the potent cytotoxicity of compounds 6 and 7, a small library of bohemamine analogs w as generated for biological evaluation by utilizing a series of aryl and alkyl aldehydes.

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“…In the absence of any catalysts or promoters, Shenvi reports that dimerization favors the formation of the stereochemical relationship corresponding to the neothiobinupharidine architecture (4:1 series 3 versus all others). [9] Thus, the principle challenge we faced was how to override the inherent diastereochemical outcome at C7 and C7′ during the formation of the thiaspirane ring.…”

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confidence: 99%

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

Korotkov

Chapman

et al. 2015

Angew Chem Int Ed

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Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1b, (−)-6,6′-dihydroxythionuphlutine (−)-2a, (−)-6,6′-dihydroxyneothiobinupharidine (−)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4a. The latter two have not been found in Nature. We have also made each of their enantiomers (−)-1a–b, (+)-2a, (+)-3a, and (−)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically-stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1a–1b—for those instances in which the NMR spectra were obtained in CD3OD—to their corresponding CD3O– adducts. Our efforts provide for the first time apoptosis data for (−)-3a, (+)-4a, and all five non-natural antipodes prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′.

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Synthesis of (−)-Neothiobinupharidine

Cited by 58 publications

References 36 publications

Synthesis of Medicinally Relevant Terpenes: Reducing the Cost and Time of Drug Discovery

Synthesis of Medicinally Relevant Terpenes: Reducing the Cost and Time of Drug Discovery

Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

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