Total Synthesis of the <i>Photorhabdus temperata</i> ssp. <i>Cinereal</i> 3240 Zwitterionic Trisaccharide Repeating Unit

Nguyen, Johny M.; Townsend, Steven D.

doi:10.1021/acs.orglett.1c02023

Cited by 7 publications

(8 citation statements)

References 26 publications

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“…Similar outcomes were observed with the hydride sources NaBH 4 and LiEt 3 BH. During our studies, a report by Townsend and co-workers identified NaBH 3 CN to be effective at reducing primary alkyl iodides . Applying analogous conditions (NaBH 3 CN, DMF, 100 °C) to our case also proved beneficial, delivering the taxol core ( 14 )confirmed by X-ray crystallographic analysisin 72% yield.…”

Section: Results and Discussionmentioning

confidence: 57%

General Synthetic Approach to Diverse Taxane Cores

et al. 2022

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Chemical synthesis of natural products is typically inspired by the structure and function of a target molecule. When both factors are of interest, such as in the case of taxane diterpenoids, a synthesis can both serve as a platform for synthetic strategy development and enable new biological exploration. Guided by this paradigm, we present here a unified enantiospecific approach to diverse taxane cores from the feedstock monoterpenoid (S)-carvone. Key to the success of our approach was the use of a skeletal remodeling strategy which began with the divergent reorganization and convergent coupling of two carvonederived fragments, facilitated by Pd-catalyzed C−C bond cleavage tactics. This coupling was followed by additional restructuring using a Sm(II)-mediated rearrangement and a bioinspired, visiblelight induced, transannular [2 + 2] photocycloaddition. Overall, this divergent monoterpenoid remodeling/convergent fragment coupling approach to complex diterpenoid synthesis provides access to structurally disparate taxane cores which have set the stage for the preparation of a wide range of taxanes.

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Section: Results and Discussionmentioning

confidence: 57%

General Synthetic Approach to Diverse Taxane Cores

et al. 2022

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“…H-phosphonates are a class of phosphonylated intermediates that have been used in the syntheses of other glycerophospholipids, including phosphatidyl inositols [ 34 , 35 , 36 , 37 ], phosphatidyl ethanolamine [ 38 ], phosphatidyl choline [ 38 ], and phosphatidyl serine [ 20 , 38 ]. They have also been used in the total synthesis of glycophospholipids [ 39 , 40 , 41 ], as well as in nucleoside-based phospholipids [ 24 ] and drugs [ 42 ]. To our surprise, they have not, however, been utilized in the synthesis of PG.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology

et al. 2022

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Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis route utilized phosphoramidite methodology that addressed issues surrounding fatty acid substrate scope and glycerol backbone modifications prior to headgroup phosphorylation, but faltered in the reproducibility of the overall pathway due to purification challenges. Herein, we present a robust pathway to optically pure PG in fewer steps, utilizing H-phosphonates that features a chromatographically friendly and stable triethyl ammonium H-phosphonate salt. Our route is also amendable to the simultaneous installation of different acyl chains, either saturated or unsaturated, on the glycerol backbone.

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“…disclosed that CA produced by the gut commensal bacteria could significantly increase the longevity of the host Caenorhabditis elegans , and this effect was conserved across different species . Attracted by the significant biological activities and the unique structures of capsular polysaccharides, a panel of glycans relevant to their repeating units have been synthesized; − notwithstanding, O -Ac-decorated oligosaccharides are rarely involved. Here we report the first chemical synthesis of a proposed CA hexasaccharide repeating unit ( 1 ).…”

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confidence: 99%