An Enantioselective Total Synthesis of (−)-Isoschizogamine

A concise enantioselective total synthesis of (−)‐isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N‐Alkylation of an enantio‐enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of piva...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2015-12, Vol.54 (49), p.14937-14940
Main Authors: Xu, Zhengren, Bao, Xu, Wang, Qian, Zhu, Jieping
Format: Article
Language:English
Subjects:
alkaloids
Alkylation
cyclizations
Enantiomers
heterocycles
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Indoles
Iodides
Irradiation
Molecular Structure
Natural products
Stereochemistry
Stereoisomerism
Synthesis
total synthesis
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Summary:A concise enantioselective total synthesis of (−)‐isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N‐Alkylation of an enantio‐enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one‐pot process leading to the formation of one CC bond and three CN bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry. Mix and go: Simply heating the alkyl iodide 1 and imine 2 afforded the hexacyclic compound 3, which was subsequently converted, in one step, into (−)‐isoschizogamine. Pivalic acid is the only reagent needed to promote this complex yet ordered domino sequence creating three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201508150