Abstract
A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3061-3068 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 6 |
| DOIs | |
| State | Published - Mar 16 2018 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Azomethine Ylide Cycloaddition Approach toward Dendrobine : Synthesis of 5-Deoxymubironine C. / Williams, Benjamin M.; Trauner, Dirk.
In: Journal of Organic Chemistry, Vol. 83, No. 6, 16.03.2018, p. 3061-3068.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Azomethine Ylide Cycloaddition Approach toward Dendrobine
T2 - Synthesis of 5-Deoxymubironine C
AU - Williams, Benjamin M.
AU - Trauner, Dirk
PY - 2018/3/16
Y1 - 2018/3/16
N2 - A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.
AB - A concise route to the azatricyclo[6.2.1.04,11]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland-Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.
UR - http://www.scopus.com/inward/record.url?scp=85044060494&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85044060494&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b00192
DO - 10.1021/acs.joc.8b00192
M3 - Article
C2 - 29490142
AN - SCOPUS:85044060494
VL - 83
SP - 3061
EP - 3068
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -