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Total Synthesis of Phenanthro‐Quinolizidine Alkaloids: (±)‐Cryptopleurine, (±)‐Boehmeriasin A, (±)‐Boehmeriasin B and (±)‐Hydroxycryptopleurine
Author(s) -
Cui Mingbo,
Wang Qingmin
Publication year - 2009
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.200900834
Subject(s) - quinolizidine , chemistry , piperidine , stereochemistry , ketone , ring (chemistry) , alkaloid , phenanthrene , nucleophilic substitution , total synthesis , pictet–spengler reaction , organic chemistry
The first synthesis of (±)‐boehmeriasin A and B and a concise synthesis of (±)‐cryptopleurine and (±)‐hydroxycryptopleurine are described. The piperidine ring of these alkaloids was constructed by the coupling of the phenanthrene ring with 2‐bromopyridine through a nucleophilic substitution reaction and subsequent reduction of the resulting pyridyl ketone. The first crystal structure of a phenanthro‐quinolizidine alkaloid is also reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)