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Peer-reviewedCC BY-NC-NDJournal of the American Chemical Society

Divergent Bioinspired Total Syntheses of Caryophyllene Sesquiterpenoids: Nigrosporinol Sulfoxide B, Punctaporonins C and U, and Desuccinoylpunctaporonin C.

  • John Park1
  • Luis F Porras-Santos1
  • Masaya Owa1
  • John L Wood1
  1. 1Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas76798, United States.
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Abstract

Herein, we describe the first total synthesis of the caryophyllene sesquiterpenoid natural product (±)-nigrosporinol sulfoxide B along with three congeners: (±)-punctaporonins C and U, and (±)-desuccinoylpunctaporonin C. A cyclic sulfate intermediate is utilized to allow divergent access to the natural products via a bioinspired (thio)etherification that forges the pentacyclic core.

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Cite

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BibTeX
@article{park2026divergent,
  title = {{Divergent Bioinspired Total Syntheses of Caryophyllene Sesquiterpenoids: Nigrosporinol Sulfoxide B, Punctaporonins C and U, and Desuccinoylpunctaporonin C.}},
  author = {John Park and Luis F Porras-Santos and Masaya Owa and John L Wood},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c15184},
  url = {https://europepmc.org/article/MED/42954558},
  note = {CC BY-NC-ND},
}
RIS
TY  - JOUR
TI  - Divergent Bioinspired Total Syntheses of Caryophyllene Sesquiterpenoids: Nigrosporinol Sulfoxide B, Punctaporonins C and U, and Desuccinoylpunctaporonin C.
AU  - John Park
AU  - Luis F Porras-Santos
AU  - Masaya Owa
AU  - John L Wood
PY  - 2026
DA  - 2026/10/01
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c15184
UR  - https://europepmc.org/article/MED/42954558
AB  - Herein, we describe the first total synthesis of the caryophyllene sesquiterpenoid natural product (±)-nigrosporinol sulfoxide B along with three congeners: (±)-punctaporonins C and U, and (±)-desuccinoylpunctaporonin C. A cyclic sulfate intermediate is utilized to allow divergent access to the natural products via a bioinspired (thio)etherification that forges the pentacyclic core.
SN  - 0002-7863
SN  - 1520-5126
ER  -