An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5
| Type of Publication: | Journal article |
| Publication status: | Published |
| Author: | Breunig, Michael; Yuan, Po; Gaich, Tanja |
| Year of publication: | 2019 |
| Published in: | Angewandte Chemie International Edition ; 2019. - ISSN 1433-7851. - eISSN 1521-3773 |
| Pubmed ID: | 31750980 |
| DOI (citable link): | https://dx.doi.org/10.1002/anie.201912613 |
| Summary: |
We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. A ring-closing metathesis as well as an auxiliary-directed 1,4-addition represent the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structure motif was established from a furanocembranoid via transannular [4+2] cycloaddition.
|
| Subject (DDC): | 540 Chemistry |
| Keywords: | furanocembranoid, norcembrenolide, ring-closing metathesis, total synthesis, transannular [4+2] cycloaddition |
| Bibliography of Konstanz: | Yes |
| Refereed: | Yes |
| Online First: Journal articles that are published online before they appear as an actual part of a journal issue. Online first articles are published on the journal's website in the publisher's version. | |
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BREUNIG, Michael, Po YUAN, Tanja GAICH, 2019. An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5. In: Angewandte Chemie International Edition. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201912613
@article{Breunig2019-11-21Unexp-47761, title={An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5}, year={2019}, doi={10.1002/anie.201912613}, issn={1433-7851}, journal={Angewandte Chemie International Edition}, author={Breunig, Michael and Yuan, Po and Gaich, Tanja} }
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