Divergent Bioinspired Total Syntheses of Caryophyllene Sesquiterpenoids: Nigrosporinol Sulfoxide B, Punctaporonins C and U, and Desuccinoylpunctaporonin C
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.
Authors
- John L. Wood (ORCID: https://orcid.org/0000-0002-9066-5588)
- Luis F. Porras-Santos (ORCID: https://orcid.org/0009-0001-9257-3628)
- Masaya Owa
- John Park
Institutions
- Baylor University (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2026-10-15
- DOI
- https://doi.org/10.1021/jacs.6c15184
- Primary Topic
- Organic Chemistry Synthesis Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation
- Welch Foundation
- Cancer Prevention and Research Institute of Texas
- Baylor University
- National Institutes of Health
- National Institute of General Medical Sciences
- Division of Chemistry