A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A
Raghavan, S; Vinoth Kumar, V
HERO ID
2901843
Reference Type
Journal Article
Year
2013
Language
English
PMID
| HERO ID | 2901843 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A |
| Authors | Raghavan, S; Vinoth Kumar, V |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 11 |
| Issue | 17 |
| Page Numbers | 2847-2858 |
| Abstract | The stereoselective synthesis of a C9-C19 fragment of the potent antitumor agent peloruside A is disclosed. The C11 stereogenic centre was created by a vinylogous Mukaiyama aldol reaction following Carreira's protocol, with excellent stereocontrol. The C13 stereogenic centre was introduced by a substrate controlled reduction. The C15 stereocentre was fashioned using Noyori's asymmetric transfer hydrogenation while the Z-trisubstituted double bond was formed by a regioselective hydrostannation of an alkyne followed by methylation of the resultant vinyl stannane using Lipshutz's protocol. The C18 chiral centre was introduced by a chemoenzymatic route. |
| Doi | 10.1039/c3ob27508f |
| Pmid | 23478973 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |