Enaminone-Based Synthesis of Dipodazine Derivatives

A series of racemic dipodazine analogues 9 were prepared in 22–80% yield from (3Z,6RS)‐3‐[(dimethylamino)methylidene]‐6‐methyl‐1‐(phenylmethyl)piperazine‐2,5‐dione (7) (Scheme 1), which was prepared in four steps from (RS)‐alanine methyl ester hydrochloride. The preparation of nonracemic 7 from (S)‐...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 89; no. 2; pp. 240 - 248
Main Authors Wagger, Jernej, Bevk, David, Meden, Anton, Svete, Jurij, Stanovnik, Branko
Format Journal Article
LanguageEnglish
Published Zürich WILEY-VCH Verlag 01.02.2006
WILEY‐VCH Verlag
Wiley
Subjects
Alkaloids
Chemistry
Chemistry, Multidisciplinary
Dipodazines
Enaminones
Indole alkaloids
Physical Sciences
Science & Technology
ACID DERIVATIVES
DIMETHYLAMINE SUBSTITUTION
SOLID-PHASE SYNTHESIS
CRYSTAL-STRUCTURE
APLYSINOPSIN-TYPE ALKALOIDS
FAMILY DENDROPHYLLIIDAE
STEREOSELECTIVE-SYNTHESIS
INDOLE ALKALOIDS
RANGE COUPLING-CONSTANTS
MARINE
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Summary:A series of racemic dipodazine analogues 9 were prepared in 22–80% yield from (3Z,6RS)‐3‐[(dimethylamino)methylidene]‐6‐methyl‐1‐(phenylmethyl)piperazine‐2,5‐dione (7) (Scheme 1), which was prepared in four steps from (RS)‐alanine methyl ester hydrochloride. The preparation of nonracemic 7 from (S)‐alanine methyl ester hydrochloride failed, since the introduction of the enamino functionality at position 3 of the precursor 6 was accompanied by almost complete racemization.
Bibliography:istex:1894DCFDD7003EEB7B5F6B39349D535E8DA2E13C
ark:/67375/WNG-VF4KW314-N
ArticleID:HLCA200690026
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200690026