Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades
T2 - application in a tag removal-cyclisation approach to spirooxindole scaffolds
AU - Coote, Susannah C.
AU - Quenum, Seidjolo
AU - Procter, David J.
PY - 2011
Y1 - 2011
N2 - A tag removal-cyclisation sequence is described that is initiated by reduction using a Sm(II) species and completed by a Sm(III) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product spirotryprostatin A.
AB - A tag removal-cyclisation sequence is described that is initiated by reduction using a Sm(II) species and completed by a Sm(III) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product spirotryprostatin A.
KW - CYCLATIVE-CAPTURE STRATEGY
KW - FLUOROUS SYNTHESIS
KW - ORGANIC-SYNTHESIS
KW - SOLID-PHASE
KW - SPIROTRYPROSTATIN-B
KW - SAMARIUM DIIODIDE
KW - PUMMERER REACTION
KW - (-)-SPIROTRYPROSTATIN B
KW - N-HETEROCYCLES
KW - SEPARATION
U2 - 10.1039/c1ob05710c
DO - 10.1039/c1ob05710c
M3 - Journal article
VL - 9
SP - 5104
EP - 5108
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 14
ER -