DOI: 10.1002/anie.200604610. Total Synthesis of (+)‐Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a <i>C</i><sub>2</sub>‐Symmetric Transition State

Total Synthesis of (+)‐Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a C2‐Symmetric Transition State

10.1002/anie.200604610

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Gagnepain, J., Castet, F., & Quideau, S. (2007). Total Synthesis of (+)âAquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the DielsâAlder Dimerization of Orthoquinols with a C2âSymmetric Transition State. Angewandte Chemie International Edition, 46(9), 1533â1535. Portico.

Authors 3

Julien Gagnepain (first)
Frédéric Castet (additional)
Stéphane Quideau (additional)

References 30 Referenced 105

10.1016/S0040-4039(98)02303-X
10.1002/3527601767.ch15
10.1039/p19740000032
For some examples of orthoquinol‐derived natural products see:
10.1016/0031-9422(91)84215-E
10.1039/P19840000095
10.1021/ja9942843
10.1021/jo048677i
10.3891/acta.chem.scand.28b-0857
10.1021/ja01481a024
10.1055/s-1990-21146
10.1021/jo01331a016
10.1021/ol026051d
10.1021/ol0349965
10.3998/ark.5550190.0004.613
10.1021/ol017068j
10.1021/ja00544a007
ThisC2‐symmetric TS is bispericyclic as it has the ideal geometry for both the [4+2] and [2+4] pathways on the basis of both the Woodward–Hoffmann (C3–C3′) and Salem–Houk (C2–C4′ and/or C2′–C4) secondary orbital interactions which also control its preference forendocycloaddition; see:
10.1021/ja016622h
10.1021/ja00167a005
10.1021/cr980364y
10.1021/ja00159a038
10.1021/ja047027t
10.1021/jo060291f
10.1021/ja00179a036
10.1021/ja00127a012

Dates

Type	When
Created	18 years, 7 months ago (Jan. 16, 2007, 11:15 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 4:05 p.m.)
Indexed	1 month ago (July 27, 2025, 3:15 a.m.)
Issued	18 years, 6 months ago (Feb. 9, 2007)
Published	18 years, 6 months ago (Feb. 9, 2007)
Published Online	18 years, 6 months ago (Feb. 9, 2007)
Published Print	18 years, 6 months ago (Feb. 19, 2007)

Funders 0

None

BibTeX

@article{Gagnepain_2007, title={Total Synthesis of (+)‐Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with a C2‐Symmetric Transition State}, volume={46}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200604610}, DOI={10.1002/anie.200604610}, number={9}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Gagnepain, Julien and Castet, Frédéric and Quideau, Stéphane}, year={2007}, month=feb, pages={1533–1535} }

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