Synthesis of the tricyclic core in stemonamine alkaloids via one-pot gold(I)-catalyzed cyclization and Schmidt rearrangement: Formal synthesis of (±)-stemonamine

Journal of Organic Chemistry

Volumn 79, Issue 22, 2014, Pages 11119-11124

  Kim, Cheoljae ^a   Kang, Soyeong ^a   Rhee, Young Ho ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; CATALYSIS; GOLD; LIGANDS; METABOLITES; NITROGEN COMPOUNDS; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL);

EFFICIENT SYNTHESIS; FORMAL SYNTHESIS; KEY REACTIONS; ONE POT; PHOSPHINE LIGANDS; SCHMIDT;

CYCLIZATION;

1 (5 ((TERT BUTYLDIPHENYLSILYL)OXY)PENT 1 EN 2 YL) 2 (PROP 2 YN 1 YL)CYCLOPENTANOL; 1 (5 AZIDOPENT 1 EN 2 YL) 2 (PROP 2 YN 1 YL)CYCLOPENTANOL; 1 (5 AZIDOPENT 1 EN 2 YL) 2 (PROP 2 YN 1 YL)CYCLOPENTYL)OXY) TRIETHYLSILANE; 1 (5 AZIDOPENT 1 EN 2 YL) 2 (PROP 2 YN 1 YL)CYCLOPENTYL)OXY)TRIMETHYLSILANE; 1 (5 HYDROXYPENT 1 EN 2 YL) 2 (PROP 2 YN 1 YL)CYCLOPENTANOL; 10 METHYLENEOCTAHYDRO 1H CYCLOPENTA[B]PYRROLO[1,2 A]AZEPIN 5(6H) ONE; 3A (3 AZIDOPROPYL) 2 METHYLENEHEXAHYDRO 1H INDEN 4(2H) ONE; 8 (3 AZIDOPROPYL) 2,3,3A,4,6,7 HEXAHYDROAZULEN 5(1H) ONE; ALKALOID DERIVATIVE; GOLD; STEMONAMINE ALKALOID; UNCLASSIFIED DRUG; ALKALOID; AZEPINE DERIVATIVE; FUSED HETEROCYCLIC RINGS; GAMMA BUTYROLACTONE; STEMONAMINE;

ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SCHMIDT REARRANGEMENT; SEQUENTIAL ANALYSIS; THIN LAYER CHROMATOGRAPHY; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ALKALOIDS; AZEPINES; CATALYSIS; CYCLIZATION; GOLD; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84912116190     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502103p     Document Type: Article

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