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Asymmetric Synthesis of the Alkaloids mayfoline and N (1)‐acetyl‐ N (1)‐deoxymayfoline
Author(s) -
Kuehne Paul,
Linden Anthony,
Hesse Manfred
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790417
Subject(s) - chemistry , enantioselective synthesis , ring (chemistry) , stereochemistry , polyamine , cleavage (geology) , recrystallization (geology) , tartrate , spermidine , conjugate , organic chemistry , catalysis , paleontology , mathematical analysis , biochemistry , geotechnical engineering , mathematics , fracture (geology) , engineering , biology , enzyme
The total syntheses of the spermidine alkaloids (−)‐mayfoline ( 11 ) and (+)‐ N (1)‐acetyl‐ N (1)‐deoxymayfoline ( 12 ) are described. These macrocyclic lactams belong to the most interesting conjugates of the polyamine derivatives very commonly found in nature. The enantioselective syntheses were achieved through resolution of the methyl 3‐amino‐3‐phenylpropanoate ( 2 ) by recrystallization of its (+)‐ L ‐tartrate salt. Construction of the 13‐membered ring ensued through condensation, reductive ring expansion (internal bond cleavage), and finally a transamidation reaction involving a second ring expansion.