| dc.contributor.author |
Sarkale, Abhijeet M. |
|
| dc.contributor.author |
Appayee, Chandrakumar |
|
| dc.date.accessioned |
2020-06-05T13:50:51Z |
|
| dc.date.available |
2020-06-05T13:50:51Z |
|
| dc.date.issued |
2020-05 |
|
| dc.identifier.citation |
Sarkale, Abhijeet M. and Appayee, Chandrakumar, “Stereodivergent synthesis of 1-hydroxymethylpyrrolizidine alkaloids”, Organic Letters, DOI: 10.1021/acs.orglett.0c01375, vol. 22, no. 11, pp. 4355-4359, May 2020. |
en_US |
| dc.identifier.issn |
1523-7060 |
|
| dc.identifier.issn |
1523-7052 |
|
| dc.identifier.uri |
http://dx.doi.org/10.1021/acs.orglett.0c01375 |
|
| dc.identifier.uri |
https://repository.iitgn.ac.in/handle/123456789/5448 |
|
| dc.description.abstract |
A first stereodivergent strategy for the asymmetric synthesis of all stereoisomers of 1-hydroxymethylpyrrolizidine alkaloids is developed using an asymmetric self-Mannich reaction as a key step. An anti-selective self-Mannich reaction of methyl 4-oxobutanoate with the PMP-amine catalyzed by a chiral secondary amine is successfully optimized for the asymmetric synthesis of (+)-isoretronecanol and (?)-isoretronecanol. A syn-selective self-Mannich reaction catalyzed by proline is utilized for the asymmetric synthesis of the diastereomer, (+)-laburnine, and its enantiomer, (?)-trachelanthamidine. |
|
| dc.description.statementofresponsibility |
by Abhijeet M. Sarkale and Chandrakumar Appayee |
|
| dc.language.iso |
en_US |
en_US |
| dc.publisher |
American Chemical Society |
en_US |
| dc.title |
Stereodivergent synthesis of 1-hydroxymethylpyrrolizidine alkaloids |
en_US |
| dc.type |
Article |
en_US |
| dc.relation.journal |
Organic Letters |
|