First Asymmetric Synthesis of Boehmeriasin A | Zendy

Dumoulin David | Zendy; Lebrun Stéphane | Zendy; Couture Axel | Zendy; Deniau Eric | Zendy; Grandclaudon Pierre | Zendy

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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

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.

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