Abstract
Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.
| Original language | English |
|---|---|
| Pages (from-to) | 4083-4088 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2014 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - 2014 |
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Keywords
- Cross-coupling
- Cycloaddition
- Michael addition
- Natural products
- Terpenoids
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
Cite this
An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction. / Wang, Yuzhou; Rogachev, Victor; Wolter, Martin; Gruner, Margit; Jäger, Anne; Metz, Peter.
In: European Journal of Organic Chemistry, Vol. 2014, No. 19, 2014, p. 4083-4088.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction
AU - Wang, Yuzhou
AU - Rogachev, Victor
AU - Wolter, Martin
AU - Gruner, Margit
AU - Jäger, Anne
AU - Metz, Peter
PY - 2014
Y1 - 2014
N2 - Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.
AB - Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.
KW - Cross-coupling
KW - Cycloaddition
KW - Michael addition
KW - Natural products
KW - Terpenoids
UR - http://www.scopus.com/inward/record.url?scp=84903315979&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84903315979&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201402165
DO - 10.1002/ejoc.201402165
M3 - Article
VL - 2014
SP - 4083
EP - 4088
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 19
ER -