Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.
Identifieur interne : 000167 ( PubMed/Curation ); précédent : 000166; suivant : 000168Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.
Auteurs : Ronan Le Goff [France] ; Ata Martin Lawson ; Adam Daïch ; Sébastien ComesseSource :
- Organic & biomolecular chemistry [ 1477-0539 ] ; 2013.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Aniline Compounds, Pyrroles, Pyrrolidines, Quinolines.
- chemical , chemistry : Aniline Compounds, Pyrroles, Pyrrolidines, Quinolines.
- Molecular Structure, Stereoisomerism.
Abstract
An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.
DOI: 10.1039/c3ob27472a
PubMed: 23400342
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pubmed:23400342Le document en format XML
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The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23400342</PMID><DateCreated><Year>2013</Year><Month>2</Month><Day>25</Day></DateCreated><DateCompleted><Year>2014</Year><Month>03</Month><Day>10</Day></DateCompleted><DateRevised><Year>2013</Year><Month>2</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1477-0539</ISSN><JournalIssue CitedMedium="Internet"><Volume>11</Volume><Issue>11</Issue><PubDate><Year>2013</Year><Month>Mar</Month><Day>21</Day></PubDate></JournalIssue><Title>Organic & biomolecular chemistry</Title><ISOAbbreviation>Org. Biomol. 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