Total Synthesis of (±)‐Phomoidride D

Leung, Joyce C.; Bedermann, Aaron A.; Njardarson, Jón T.; Spiegel, David A.; Murphy, Graham K.; Hama, Naoto; Twenter, Barry M.; Dong, Ping; Shirahata, Tatsuya; McDonald, Ivar M.; Inoue, Munenori; Taniguchi, Nobuaki; McMahon, Travis C.; Schneider, Christopher; Tao, Nancy; Stoltz, Brian M.; Wood, John L.

doi:10.1002/anie.201712369

Cited by 33 publications

(16 citation statements)

References 33 publications

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“… [19] Lastly, palladium mediated carbonylation of β‐keto ester IX derived enol triflates represents a powerful method for the direct access of anhydride moieties. [20] This sequence was successfully applied in Wood's synthesis of phomoidride D. [21] …”

Section: Resultsmentioning

confidence: 99%

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

Wildermuth

Steinborn

Barber

et al. 2021

Chemistry A European J

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Herein is given a full account of the evolution of the first total synthesis of (+)‐cornexistin. Initial efforts were based on masking the reactive maleic anhydride moiety as a 3,4‐substituted furan and on forming the nine‐membered carbocycle in an intramolecular Conia‐ene or Nozaki–Hiyama–Kishi (NHK) reaction. Those strategies suffered from low yields and were jeopardized by a late‐stage installation of the Z‐alkene, as well as the stereocenters along the eastern periphery. These issues were addressed by employing a chiral‐pool strategy that involved construction of the crucial stereocenters at C2, C3 and C8 at an early stage with installation of the maleic anhydride as late as possible. The successful approach featured an intermolecular NHK coupling to install the Z‐alkene, a syn‐Evans‐aldol reaction to forge the stereocenters along the eastern periphery, an intramolecular allylic alkylation to close the nine‐membered carbocycle, and a challenging stepwise hydrolysis of a β‐keto nitrile to furnish the maleic anhydride.

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Section: Resultsmentioning

confidence: 99%

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

Wildermuth

Steinborn

Barber

et al. 2021

Chemistry A European J

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“…Another prime example of a cascade reaction employing a ketyl radical generated by SmI 2 comes from the 2018 total synthesis of (±)-phomoidride D ( 218 ) by Wood and co-workers ( Scheme 32 ). 54 Treatment of ketone 216 with SmI 2 triggered a 5- endo -trig/5- exo -tet cyclization sequence; 5- endo -trig cyclization of ketyl radical 219 , followed by reduction, and an unusual intramolecular alkylation of an organosamarium ( 221 ), delivered advanced intermediate 217 .…”

Section: Ketyl Radicals In Natural Product Synthesismentioning

confidence: 99%

Recent advances in the chemistry of ketyl radicals

et al. 2021

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“…While the phenolic oxidation (97→100) sets the stage for the cycloaddition to occur, the stereocenters of the skeleton were installed by the Diels-Alder reaction (100→101). 47 Template for SYNTHESIS © Thieme Stuttgart • New York 2021-06-04 page 8 of 20…”

Section: Total Synthesis Of (±)-Phomoidride Dmentioning

confidence: 99%

“…the stage for the cycloaddition to occur, the stereocenters of the skeleton were installed via a Diels-Alder reaction (100 → 101). 47…”

Section: Special Topic Synthesismentioning

confidence: 99%

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

et al. 2021

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The Diels-Alder reaction has long established its high rank in the toolbox of any natural product chemist. The tremendous toleration of building blocks of various complexity and derivatization degree, as well as the enablement of furnishing six-membered rings with well-defined stereochemistry represents its main features and advantages. In recent years, many total syntheses of natural products relied at some point on the use of a [4+2]-cycloaddition step. Among classic approaches, several modifications of the Diels-Alder reaction, such as hetero-Diels-Alder reactions, dehydro-Diels-Alder reactions or domino-Diels-Alder reactions have been employed to extend the scope in the synthesis of natural products. Our review covers the application of the Diels-Alder reaction in natural product syntheses from 2017 to 2020, as well as selected methodologies which were inspired by, or could be used to access natural products.

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Total Synthesis of (±)‐Phomoidride D

Cited by 33 publications

References 33 publications

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

Recent advances in the chemistry of ketyl radicals

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

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