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Total Synthesis of the Cytotoxic Guaipyridine Sesquiterpene Alkaloid (+)‐Cananodine
Author(s) -
Craig Donald,
Henry Gavin D.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600414
Subject(s) - chemistry , total synthesis , sesquiterpene , stereochemistry , ring closing metathesis , metathesis , claisen rearrangement , alkaloid , olefin metathesis , salt metathesis reaction , enantioselective synthesis , pyridine , organic chemistry , catalysis , polymerization , polymer
Abstract The enantiospecific total synthesis of the cytotoxic guaipyridine sesquiterpene alkaloid (+)‐cananodine ( 1 ) is described. A chiral pool/chiral auxiliary based approach is described for the synthesis of a key oxazolidinone intermediate. Subsequent key steps involve diastereoselective oxazolidinone allylation, cycloheptenylmethanol formation using ring‐closing olefin metathesis, microwave‐assisted decarboxylative Claisen rearrangement reaction, and use of a novel pyridine‐forming method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)