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Synthesis of the Spermidine Alkaloid (−)‐(4 R )‐Dihydroisomyricoidine
Author(s) -
Horni Albert,
Linden Anthony,
Hesse Manfred
Publication year - 1998
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.19980810541
Subject(s) - chemistry , spermidine , wittig reaction , side chain , stereochemistry , alkaloid , derivative (finance) , optically active , lactam , michael reaction , organic chemistry , catalysis , polymer , financial economics , economics , enzyme
An asymmetric synthesis of (−)‐(4 R )‐dihydroisomyricoidine ( 28 ), a 13‐membered amino lactam of type A, was performed by a diastereoselective Michael addition between the spermidine derivative 3 and the commercially available optically active ethyl carboxylate 4 , and the cyclization of the resulting ω‐amino acid 7 using diethyl phosphorocyanidate ((EtO) 2 POCN), followed by a Wittig reaction to introduce the ( Z )‐side chain. Some side reactions are also discussed.