New routes to clavine-type ergot alkaloids. Part 2: Synthesis of the last, so far not yet synthesized member of the clavine alkaloid family, (±)-cycloclavine

Starting from 4-bromo-Uhle's ketone ( 2), an alkylation step using ethyl 3-methylamino-propionate followed by intramolecular aldol condensation in two steps, transformation of the ester group into a methyl group, and finally cyclopropanation of the 8,9 double bond, resulted in a six-step total...

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Bibliographic Details
Published inTetrahedron Vol. 64; no. 13; pp. 2924 - 2929
Main Authors Incze, Mária, Dörnyei, Gábor, Moldvai, István, Temesvári-Major, Eszter, Egyed, Orsolya, Szántay, Csaba
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.03.2008
Elsevier
Subjects
(±)-Cycloclavine
Chemistry
Chemistry, Organic
Clavine alkaloids
Cyclopropanation with diazomethane
Modified intramolecular Reformatsky-type cyclization
Physical Sciences
Science & Technology
Total synthesis from 4-bromo-Uhle's ketone
Modified intramolecular Reformatsky-type cyclization
(±)-Cycloclavine
Clavine alkaloids
Cyclopropanation with diazomethane
Total synthesis from 4-bromo-Uhle's ketone
clavine alkaloids
modified intramolecular Reformatsky-type cyclization
ASPERGILLUS-JAPONICUS
CYCLOCLAVINE
(+/-)-cycloclavine
cyclopropanation with diazomethane
total synthesis from 4-bromo-Uhle's ketone
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Summary:Starting from 4-bromo-Uhle's ketone ( 2), an alkylation step using ethyl 3-methylamino-propionate followed by intramolecular aldol condensation in two steps, transformation of the ester group into a methyl group, and finally cyclopropanation of the 8,9 double bond, resulted in a six-step total synthesis of (±)-cycloclavine ( 1). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.01.101