Synthetic Strategies toward the Guaiane Sesquiterpene Englerin A

Chain, William J.

doi:10.1055/s-0030-1289521

Cited by 25 publications

(10 citation statements)

References 10 publications

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“…Several recent reviews nicely summarize the current status of englerins. [xi] Our continuous interest in exploring natural products from ethnomedicine as medicinal leads [xii] has prompted us to design an enantioselective strategy toward englerins. [xiii] In this account we describe in detail the results of our efforts and the biological evaluation of structurally simplified englerin analogues.…”

Section: Introductionmentioning

confidence: 99%

Formal Synthesis of (−)‐Englerin A and Cytotoxicity Studies of Truncated Englerins

Xu¹,

Caro‐Diaz²,

Batova³

et al. 2012

Chemistry An Asian Journal

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An efficient formal synthesis of (−)-englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell lines. The developed strategy proceeds in an enantioselective manner by constructing the BC ring system of 1 via a Rh(II)-catalyzed [4+3] cycloaddition and subsequently attaching the A ring via an intramolecular aldol condensation reaction. As such, this strategy allows the synthesis of truncated englerins. Evaluation of these analogues in A498 renal cancer cell line suggests that the A ring of englerin is crucial to its antiproliferative activity. Moreover, evaluation of these analogues led to the identification of potent growth inhibitors of CEM cells with GI50 values ranging from 1–3 μM.

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Section: Introductionmentioning

confidence: 99%

Formal Synthesis of (−)‐Englerin A and Cytotoxicity Studies of Truncated Englerins

Xu¹,

Caro‐Diaz²,

Batova³

et al. 2012

Chemistry An Asian Journal

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“…The initial flurry of interest in the synthesis of this fascinating molecule has culminated in five total syntheses and one formal synthesis in the short time span since its isolation 61. As described, these syntheses have expanded the realms of possibility in the field, and stand as exemplars of elegance and evolution in synthetic strategy.…”

Section: Discussionmentioning

confidence: 99%

Chemical Synthesis of the Englerins

Pouwer

Richard

Tseng

et al. 2011

Chemistry An Asian Journal

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In the long lasting battle against cancer, Nature sometimes gives a helping hand to researchers to find new drugs for the treatment of diseases and improvement of patients' well-being. Englerin A has emerged as a promising anticancer candidate as well as being an exciting synthetic challenge for organic chemists. This focus review summarizes the total syntheses reported to date and the synthetic approaches toward analogues of this fascinating natural product.

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“…Our synthesis of (−)‐englerins 60 a – b and that reported by the group of Ma were based on our previous synthesis of (+)‐orientalol. The synthesis developed by our group started from known chiral 1,6‐enyne 67 , readily available in three steps from geraniol in a 95 : 5 enantiomeric ratio (Scheme ).…”

Section: Cascade Cyclizations Of Functionalized 1n‐enynesmentioning

confidence: 99%

Gold(I)‐Catalysis for the Synthesis of Terpenoids: From Intramolecular Cascades to Intermolecular Cycloadditions

Mayans

Armengol-Relats

Calleja

et al. 2018

Israel Journal of Chemistry

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Gold(I)‐catalyzed cycloisomerizations of 1,n‐enynes proceed through electrophilic intermediates that can be trapped intra‐ or intermolecularly by a variety of hetero‐ and carbon nucleophiles to form complex skeletons in a single step. This review covers the efforts of our group towards the development of new reactions that have been successfully applied in the total synthesis of several natural terpenoids and related carbocyclic structures, as well as for the ready access to challenging linear acenes.

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Synthetic Strategies toward the Guaiane Sesquiterpene Englerin A

Cited by 25 publications

References 10 publications

Formal Synthesis of (−)‐Englerin A and Cytotoxicity Studies of Truncated Englerins

Formal Synthesis of (−)‐Englerin A and Cytotoxicity Studies of Truncated Englerins

Chemical Synthesis of the Englerins

Gold(I)‐Catalysis for the Synthesis of Terpenoids: From Intramolecular Cascades to Intermolecular Cycloadditions

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