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Reactions with indole derivatives, LIV. Enantioselective total synthesis of (19 Z )‐geissoschizine and of (16 R ,19 Z )‐ and (16 S ,19 Z )‐isositsirikine
Author(s) -
Winterfeldt Ekkehard,
Freund Ralf
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860712
Subject(s) - chemistry , enantioselective synthesis , indole test , stereochemistry , sodium , total synthesis , medicinal chemistry , reduction (mathematics) , organic chemistry , catalysis , geometry , mathematics
Starting from the easily available, enantiomerically pure lactam 2 (19 Z )‐geissoschizine ( 9 ) is prepared. On sodium tetrahydroborate reduction 9 is transformed into (16 R ,19 Z )‐ and (16 S ,19 Z )‐isositsirikine 5 .