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Total Synthesis of (−)‐Strychnine via the Wieland–Gumlich Aldehyde
Author(s) -
Solé Daniel,
Bonjoch Josep,
GarcíaRubio Silvina,
Peidró Emma,
Bosch Joan
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990201)38:3<395::aid-anie395>3.0.co;2-5
Subject(s) - enantiopure drug , indoline , enantioselective synthesis , strychnine , piperidine , total synthesis , strychnos , aldehyde , heck reaction , ring (chemistry) , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , alkaloid , catalysis , palladium , biochemistry
Fifteen steps suffice for an enantioselective total synthesis of (−)‐strychnine ( 1 ) from 1,3‐cyclohexanedione. The key steps are the easy generation of the enantiopure intermediate 2 , the closure of the piperidine ring by a reductive Heck reaction, and the elaboration of the indoline nucleus in an advanced synthetic stage. TBDMS= tert ‐butyldimethylsilyl.