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Total synthesis of (+)-erogorgiaene using lithiation-borylation methodology, and stereoselective synthesis of each of its diastereoisomers.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Elford, Tim G. Nave, Stefan Sonawane, Ravindra P. Aggarwal, Varinder K. |
| Copyright Year | 2011 |
| Abstract | A short (8 steps) synthesis of (+)-erogorgiaene in 44% overall yield from p-methylacetophenone is described. Key steps include lithiation/borylation-protodeboronation to build up the molecule and control the stereochemistry at C1 and C4. The C11 stereochemistry was similarly set up by using lithiation/borylation methodology. The use of a mixed, unhindered borane in the lithiation/borylation reaction proved critical to success in the reaction of the tetralone-derived carbamate to control the C4 stereochemistry. The power of the reagent controlled methodology is illustrated in the stereocontrolled synthesis of all of the diastereomers of (+)-erogorgiaene. |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/ja207869f |
| PubMed reference number | 21936552 |
| Journal | Medline |
| Volume Number | 133 |
| Issue Number | 42 |
| Alternate Webpage(s) | http://www.chm.bris.ac.uk/org/aggarwal/docs/publications/2012synfacts80.pdf |
| Alternate Webpage(s) | http://www.chm.bris.ac.uk/org/aggarwal/docs/publications/2011jacs16798.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/ja207869f |
| Journal | Journal of the American Chemical Society |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
