Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

Adams, Gregory L.; Carroll, Patrick J.; Smith, Amos B.

doi:10.1021/ja3111626

Cited by 107 publications

(39 citation statements)

References 76 publications

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“…In addition, its unusual [2.2.2] bicyclic lactone moiety provides a unique synthetic challenge in akuammiline alkaloid total synthesis. The valiant efforts of the groups of Smith [32] and Snyder [33] have recently led to two completed total syntheses, both of which harness the power of cascade reactions to access (+)-14.…”

Section: Total Syntheses Of (+)-Scholarisine Amentioning

confidence: 99%

“…[24] Although many akuammiline alkaloids have yet to succumb to laboratory synthesis, synthetic efforts spanning the past five years have led to the completed total syntheses of four daunting akuammilines: (À)-vincorine [(À)-15], [25,26,27] (À)-aspidophylline A [(À)-4], [28,29,30] (À)-picrinine [(À)-13], [31] and (+)-scholarisine A [(+) -14]. [32,33] Although the synthetic routes towards these alkaloids contain a variety of creative elements, one unifying theme is their utilization of innovative cascade reactions to elegantly and efficiently forge their intricate architectures. This minireview provides a perspective on the key transformations which construct multiple chemical bonds in one process, and how these cascades have fuelled achievements in akuammiline total synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

et al. 2014

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The akuammiline alkaloids are a family of intricate natural products which have received considerable attention from scientists worldwide. Despite the fact that many members of this alkaloid class were discovered over 50 years ago, synthetic chemistry has been unable to address their architectures until recently. This minireview provides a brief overview of the rich history of the akuammiline alkaloids, including their isolation, structural features, biological activity, and proposed biosyntheses. Furthermore, several recently completed total syntheses are discussed in detail. These examples not only serve to highlight modern achievements in alkaloid total synthesis, but also demonstrate how the molecular scaffolds of the akuammilines have provided inspiration for the discovery and implementation of innovative cascade reactions for the rapid assembly of complex structures.

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Section: Total Syntheses Of (+)-Scholarisine Amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

et al. 2014

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“…Over the past decades, akuammilinea lkaloids have interested the synthetic community owing to their unique chemical structure and biological activity. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] In particular,s trictamine (1)w as first synthesized in 2015 and 2016 by the groups of Garg (enantioselective), [18] Zhu (racemic), [19] Ohno (formal), [20] and ours (formal). [21] Biosynthetically,s trictamine (1)b elongs to the group of monoterpenoid indole alkaloids, which are derived from (E)-geissoschizine (4).…”

Section: Introductionmentioning

confidence: 99%

Formal Total Synthesis of (±)‐Strictamine by [2,3]‐Sigmatropic Stevens Rearrangements

Eckermann

Breunig

Gaich

2017

Chemistry A European J

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To date, more than 100 congeners of the akuammiline alkaloid family have been isolated. Their signature structural element is a methanoquinolizidine moiety, a cage-like scaffold structurally related to adamantane. The structural variations of the family members originate from oxidative processes that mostly trigger rearrangements of the methanoquinolizidine motif. The family of the akuammiline alkaloids is best represented by strictamine. It bears the least functionalized carbon skeleton of all family members without lacking the signature structural motifs. Herein, we report the formal synthesis of strictamine through a Stevens [2,3]-sigmatropic rearrangement as a key step and the synthetic pitfalls related with its synthesis.

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“…Except for DNA demethylation15, Tet1 also works in various ways and crosstalks with partners to regulate gene expression and cancer161718192021. Vitamin C (Vc) is important in Tet1 activity522, calpain could mediate TET1 degradation23, and promoted glycosylation of chromatin by binding to O-N acetyl glucose transferase (OGT) and mediate posttranscriptional modification2425.…”

mentioning

confidence: 99%

The Modification of Tet1 in Male Germline Stem Cells and Interact with PCNA, HDAC1 to promote their Self-renewal and Proliferation

Zheng

Zhai

et al. 2016

Sci Rep

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Epigenetic modification plays key roles in spermatogenesis, especially DNA methylation dynamic is important in sustaining normal spermatogenesis. Ten-eleven translocation 1 (Tet1) is not only a key demethylase, which works in specific gene regions, but also crosstalks with partners to regulate epigenetic progress as protein complexes. Dairy goat is an important livestock in China, while the unstable culture system in vitro inhibits optimization of new dairy goat species. The study of epigenetic modification in male germline stem cells (mGSCs) is beneficial to the optimization of adult stem cell culture system in vitro, and the improvement of sperm quality and breeding of selected livestock. In our study, we not only analyzed the morphology, gene expression, DNA methylation and histone methylation dynamic in mouse Tet1 (mTet1) modified mGSCs, we also analyzed the stemness ability by in vivo transplantation and explored the functional mechanism of Tet1 in dairy goat mGSCs. The results showed mTet1 modified mGSCs had better self-renewal and proliferation ability than wild-type mGSCs, mTet1 could also up-regulate JMJD3 to decrease H3K27me3, which also showed to suppress the MEK-ERK pathway. Furthermore, Co-IP analysis demonstrated that TET1 interact with PCNA and HDAC1 by forming protein complexes to comprehensively regulate dairy goat mGSCs and spermatogenesis.

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Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

Cited by 107 publications

References 76 publications

Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

Formal Total Synthesis of (±)‐Strictamine by [2,3]‐Sigmatropic Stevens Rearrangements

The Modification of Tet1 in Male Germline Stem Cells and Interact with PCNA, HDAC1 to promote their Self-renewal and Proliferation

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