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Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A

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2021

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Journal of the American Chemical Society. American Chemical Society (ACS). 2021, 143(31), pp. 11934-11938. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/jacs.1c05257

Zusammenfassung

The first asymmetric synthesis of pepluanol A (1) is presented. The synthesis route is very concise (10 steps) and features a Curtin-Hammett-driven stereoconvergent intramolecular Diels-Alder reaction. A Nozaki-Hiyama-Kishi reaction comprises the connective step, bringing together the seven-membered enone system bearing the dienophile and the diene in the side chain. Subsequent stereoconvergent IMDA reaction furnishes the carboskeleton of the natural product in only 7 steps. The reactions were carried out on a gram scale up to an advanced intermediate and including the stereoconvergent intramolecular Diels-Alder reaction.

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Fachgebiet (DDC)
540 Chemie

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Anions,Aldehydes,Chemical reactions,Oxidation,Molecular structure

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ISO 690YUAN, Po, Christa K. G. GERLINGER, Jan HERBERGER, Tanja GAICH, 2021. Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A. In: Journal of the American Chemical Society. American Chemical Society (ACS). 2021, 143(31), pp. 11934-11938. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/jacs.1c05257
BibTex
@article{Yuan2021-08-11TenSt-54736,
  year={2021},
  doi={10.1021/jacs.1c05257},
  title={Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A},
  number={31},
  volume={143},
  issn={0002-7863},
  journal={Journal of the American Chemical Society},
  pages={11934--11938},
  author={Yuan, Po and Gerlinger, Christa K. G. and Herberger, Jan and Gaich, Tanja}
}
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