Total Synthesis of Phenanthro‐Quinolizidine Alkaloids: (±)‐Cryptopleurine, (±)‐Boehmeriasin A, (±)‐Boehmeriasin B and (±)‐Hydroxycryptopleurine | Zendy

Cui Mingbo | Zendy; Wang Qingmin | Zendy

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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)

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