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Peer-reviewedCC BY 4.0Journal of the American Chemical Society

Simultaneous Installation of 1,6-Stereocenters by Asymmetric Allylation of Resorcinol Boronates: Application to the Synthesis of Merocyclophane A

  • Ze-Shu Wang1
  • Joshua D. Mitchell1
  • Jasper L. Tyler1
  • Laura J. McCormick McPherson2
  • Simon J. Coles2
  • Varinder K. Aggarwal1
  1. 1School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, U.K.
  2. 2UK National Crystallography Service, Department of Chemistry, University of Southampton, Highfield Campus, Southampton SO17 1BJ, U.K.
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Abstract

Installing multiple noncontiguous stereocenters in a single catalytic event offers a powerful platform for constructing complex three-dimensional molecular architectures, yet asymmetric methodologies capable of selectively forging remote 1,n-stereochemical relationships remain limited. Here we disclose a strategy for the simultaneous installation of 1,6-stereocenters via para-selective activation of chiral resorcinol boronates with π-allyl iridium complexes. Upon oxidation-induced rearomatization, the resulting dearomatized intermediates furnish the allylated products in an overall transformation that exhibits excellent regio- and stereoselectivity. Crucially, independent variation of the ligand and boronic ester configuration provides predictable access to all four stereoisomers with no observable match–mismatch effects. The synthetic potential of the methodology is exemplified by a concise total synthesis of the cyanobacteria-derived [7.7]­paracyclophane merocyclophane A, in which all stereocenters are installed simultaneously on the resorcinol core in a single step.

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Cite

BibTeXRIS
BibTeX
@article{wang2026simultaneous,
  title = {{Simultaneous Installation of 1,6-Stereocenters by Asymmetric Allylation of Resorcinol Boronates: Application to the Synthesis of Merocyclophane A}},
  author = {Ze-Shu Wang and Joshua D. Mitchell and Jasper L. Tyler and Laura J. McCormick McPherson and Simon J. Coles and Varinder K. Aggarwal},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c14045},
  url = {https://doi.org/10.1021/jacs.6c14045},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Simultaneous Installation of 1,6-Stereocenters by Asymmetric Allylation of Resorcinol Boronates: Application to the Synthesis of Merocyclophane A
AU  - Ze-Shu Wang
AU  - Joshua D. Mitchell
AU  - Jasper L. Tyler
AU  - Laura J. McCormick McPherson
AU  - Simon J. Coles
AU  - Varinder K. Aggarwal
PY  - 2026
DA  - 2026/10/22
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c14045
UR  - https://doi.org/10.1021/jacs.6c14045
AB  - Installing multiple noncontiguous stereocenters in a single catalytic event offers a powerful platform for constructing complex three-dimensional molecular architectures, yet asymmetric methodologies capable of selectively forging remote 1,n-stereochemical relationships remain limited. Here we disclose a strategy for the simultaneous installation of 1,6-stereocenters via para-selective activation of chiral resorcinol boronates with π-allyl iridium complexes. Upon oxidation-induced rearomatization, the resulting dearomatized intermediates furnish the allylated products in an overall transformation that exhibits excellent regio- and stereoselectivity. Crucially, independent variation of the ligand and boronic ester configuration provides predictable access to all four stereoisomers with no observable match–mismatch effects. The synthetic potential of the methodology is exemplified by a concise total synthesis of the cyanobacteria-derived [7.7]­paracyclophane merocyclophane A, in which all stereocenters are installed simultaneously on the resorcinol core in a single step.
SN  - 0002-7863
SN  - 1520-5126
ER  -