Use of the intramolecular heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (±)-gelsemine

Journal of the American Chemical Society

Volumn 127, Issue 51, 2005, Pages 18054-18065

  Madin, Andrew ^a,b   O'Donnell, Christopher J ^a,c   Oh, Taeboem ^a,d   Old, David W ^a,e   Overman, Larry E ^a   Sharp, Matthew J ^a,f  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^c PFIZER INC   (United States)

^d CALIFORNIA STATE UNIVERSITY   (United States)

^e ALLERGAN INC   (United States)

^f GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EQUATORIAL ALCOHOL; GELSEMINE; PENTACYCLIC PRODUCT; SKELETAL REARRANGEMENT;

CARBON;

2 BROMOETHYLAMINE; 2 HALOANILIDE; ALCOHOL; ALKALOID; ANILIDE; AZATRICYCLO[4.4.0.0]DECANONE; AZIRIDINE DERIVATIVE; CARBON; DECANOIC ACID DERIVATIVE; GELSEMINE; INDOLE DERIVATIVE; N METHOXYCARBONYL BETA BROMOETHYLAMINE; PHOSPHATE; SILVER DERIVATIVE; SPIROOXINDOLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

ALKALOIDS; INDOLES; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 29844449086     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055711h     Document Type: Article

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