Stereocontrolled synthesis of (±)-deoxypodophyllotoxin via the benzyl equivalent of the Peterson reaction

Takano, Seiichi; Otaki, Shizuo; Ogasawara, Kunio

doi:10.1039/c39850000485

Cited by 14 publications

(2 citation statements)

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“…Next, we focused on two chemicals, C‐157 and D‐572, which showed the greatest inhibitory effects on cancer cell invasion. Compound C‐157 is revealed as deoxypodophyllotoxin (DPT) and D‐572 is an indole alkaroid (Fig. a).…”

Section: Resultsmentioning

confidence: 99%

Identification of anti‐cancer chemical compounds using Xenopus embryos

et al. 2016

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Cancer tissues have biological characteristics similar to those observed in embryos during development. Many types of cancer cells acquire pro‐invasive ability through epithelial–mesenchymal transition (EMT). Similar processes (gastrulation and migration of cranial neural crest cells [CNCC]) are observed in the early stages of embryonic development in Xenopus during which cells that originate from epithelial sheets through EMT migrate to their final destinations. The present study examined Xenopus embryonic tissues to identify anti‐cancer compounds that prevent cancer invasion. From the initial test of known anti‐cancer drugs, AMD3100 (an inhibitor of CXCR4) and paclitaxel (a cytoskeletal drug targeting microtubules) effectively prevented migration during gastrulation or CNCC development. Blind‐screening of 100 synthesized chemical compounds was performed, and nine candidates that inhibited migration of these embryonic tissues without embryonic lethality were selected. Of these, C‐157 (an analog of podophyllotoxin) and D‐572 (which is an indole alkaroid) prevented cancer cell invasion through disruption of interphase microtubules. In addition, these compounds affected progression of mitotic phase and induced apoptosis of SAS oral cancer cells. SAS tumors were reduced in size after intratumoral injection of C‐157, and peritoneal dissemination of melanoma cells and intracranial invasion of glioma cells were inhibited by C‐157 and D‐572. When the other analogues of these chemicals were compared, those with subtle effect on embryos were not tumor suppressive. These results suggest that a novel chemical‐screening approach based on Xenopus embryos is an effective method for isolating anti‐cancer drugs and, in particular, targeting cancer cell invasion and proliferation.

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Section: Resultsmentioning

confidence: 99%

Identification of anti‐cancer chemical compounds using Xenopus embryos

et al. 2016

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“…[55][56][57][58][59][60] For this reason a number of approaches have used simple symmetrical maleate systems exploiting the greater accessibility of the C3 carbonyl group for subsequent selective epimerisation and reduction of the cycloadduct. [61,62] The particular problems of fumarate cycloadditions are illustrated by the early work of Durst (Scheme 16). [63] In this, an o-quinodimethide is generated and trapped in a photo-enolisation Diels-Alder strategy.…”

Section: C-ring Formation By Cycloaddition Reactionsmentioning

confidence: 99%

Advances in the Synthesis of Aryltetralin Lignan Lactones

Sellars

Steel

2007

Eur J Org Chem

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Etoposide and tenoposide, derivatives of the aryltetralin lignan lactone podophyllotoxin (5), are clinically important anticancer agents. The structure of podophyllotoxin includes four contiguous chiral centres contained within a stereochemically unstable trans‐fused tetrahydronaphthalene lactone skeleton. Reflecting this challenging structure and important biological role there has been long‐standing interest in developing efficient stereocontrolled syntheses of this class of natural product. This microreview summarises the key developments towards this end focussing on more recent developments both from within the authors group and elsewhere.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Peterson Olefination

2010

Comprehensive Organic Name Reactions and Reagents

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The two‐step synthesis of olefin involving the addition of an α‐silyl carbanion to a carbonyl compound to form β‐silyl alcohol and the elimination of silol is generally known as the Peterson olefination. This reaction has many advantages. This reaction has been modified by the use of an α‐silyl selenoacetamide to generate E ‐olefins. Furthermore, an asymmetric version of this reaction has been developed by the use of an external chiral tridentate amino diether as a chiral ligand. This reaction has been generally applied in the preparation of olefins.

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Stereocontrolled synthesis of (±)-deoxypodophyllotoxin via the benzyl equivalent of the Peterson reaction

Cited by 14 publications

References 0 publications

Identification of anti‐cancer chemical compounds using Xenopus embryos

Identification of anti‐cancer chemical compounds using Xenopus embryos

Advances in the Synthesis of Aryltetralin Lignan Lactones

Peterson Olefination

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