A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels-Alder Reaction

Masked talent: A tetracyclo[5.3.3.04,9.04,12]tridecane skeleton can be accessed by an intramolecular reverse‐electron‐demand Diels–Alder (REDDA) reaction of masked ortho‐benzoquinone (MOB; see scheme). This reaction gives access to the pentacyclic framework of atropurpuran, and also enables the cons...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 39; pp. 9177 - 9179
Main Authors Suzuki, Takahiro, Sasaki, Aya, Egashira, Naoki, Kobayashi, Susumu
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 19.09.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Aconitum - chemistry
Alkanes - chemistry
benzoquinones
Benzoquinones - chemistry
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Cyclization
Diels-Alder reaction
Diterpenes - chemical synthesis
Diterpenes - chemistry
Electrons
Molecular Conformation
pentacycles
Physical Sciences
Science & Technology
synthetic methods
terpenoids
pentacycles
ORGANIC-SYNTHESIS
benzoquinones
terpenoids
Diels-Alder reaction
synthetic methods
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Summary:Masked talent: A tetracyclo[5.3.3.04,9.04,12]tridecane skeleton can be accessed by an intramolecular reverse‐electron‐demand Diels–Alder (REDDA) reaction of masked ortho‐benzoquinone (MOB; see scheme). This reaction gives access to the pentacyclic framework of atropurpuran, and also enables the construction of other anti‐Bredt and cage‐like complex molecules.
Bibliography:ArticleID:ANIE201103950
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istex:56050E9BD2A042D2BBF25C0FA6AB4F954CE1310C
This research was supported in part by a Grant-in-Aid for Young Scientists (B, KAKENHI no. 22790022) from the Japan Society for the Promotion of Science. We thank Prof. K. Miyamura and K. Ueji (Department of Chemistry, Tokyo University of Science) for assistance with X-ray analysis.
Grant-in-Aid for Young Scientists - No. 22790022
This research was supported in part by a Grant‐in‐Aid for Young Scientists (B, KAKENHI no. 22790022) from the Japan Society for the Promotion of Science. We thank Prof. K. Miyamura and K. Ueji (Department of Chemistry, Tokyo University of Science) for assistance with X‐ray analysis.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103950