Regioselective 6-Endo Cyclizations of 2-Indolylacyl Radicals:  Total Synthesis of the Pyrido[4,3-b]carbazole Alkaloid Guatambuine

A regioselective 6-endo reductive cyclization of 2-indolylacyl radicals constitutes the key step of a straightforward synthetic entry to the olivacine skeleton, illustrated by a total synthesis of the tetrahydropyridine alkaloid guatambuine.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 71; no. 4; pp. 1746 - 1749
Main Authors Bennasar, M.-Lluïsa, Roca, Tomàs, Ferrando, Francesc
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.02.2006
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Chemistry
Chemistry, Organic
Cyclization
Ellipticines - chemical synthesis
Exact sciences and technology
Free Radicals
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indole Alkaloids - chemical synthesis
Indoles - chemistry
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ENTRY
HETEROCYCLES
OLIVACINE
CONSTRUCTION
ELLIPTICINE
CHEMISTRY
INTRAMOLECULAR REACTIONS
SKELETON
Chemical reduction
Endo stereoisomer
Alkaloid
Cyclization
Regioselectivity
Nitrogen heterocycle
Organic free radical
Chemical synthesis
Total synthesis
Pyridine derivatives
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Summary:A regioselective 6-endo reductive cyclization of 2-indolylacyl radicals constitutes the key step of a straightforward synthetic entry to the olivacine skeleton, illustrated by a total synthesis of the tetrahydropyridine alkaloid guatambuine.
Bibliography:ark:/67375/TPS-L4RHZRTC-V
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo052428s