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First Asymmetric Synthesis of Boehmeriasin A
Author(s) -
Dumoulin David,
Lebrun Stéphane,
Couture Axel,
Deniau Eric,
Grandclaudon Pierre
Publication year - 2010
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.200901404
Subject(s) - pyrrolidine , piperidine , chemistry , stereochemistry , acylation , natural product , metathesis , ring closing metathesis , radical cyclization , aldol reaction , nucleophile , aldol condensation , sequence (biology) , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization , biochemistry
Abstract The first asymmetric synthesis of phenanthroquinolizidinealkaloid ( R )‐boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate ( RS , R )‐ 4 were achieved through a combination of highly diastereoselective 1,2‐nucleophilic addition on (–)‐( S )‐1‐amino‐2‐(methoxymethyl)pyrrolidine hydrazones with a ring‐closing metathesis to ensure the construction of the piperidine template. A subsequent acylation/oxidation/aldol condensation/radical cyclization sequence completed the assembly of the title ( R )‐configured natural product.