Synthesis of the Spermidine Alkaloid (−)‐(4 R )‐Dihydroisomyricoidine | Zendy

Horni Albert | Zendy; Linden Anthony | Zendy; Hesse Manfred | Zendy

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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.

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