Total Synthesis of (+)-Haplophytine

Advancing alkaloid synthesis: (+)‐Haplophytine (see structure) was the target of a total synthesis featuring a highly stereoselective intramolecular Mannich reaction, Friedel–Crafts alkylation, oxidative rearrangement, and Fischer indole synthesis.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 48; no. 41; pp. 7600 - 7603
Main Authors Ueda, Hirofumi, Satoh, Hitoshi, Matsumoto, Koji, Sugimoto, Kenji, Fukuyama, Tohru, Tokuyama, Hidetoshi
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 28.09.2009
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
alkaloids
Chemistry
Chemistry, Multidisciplinary
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Mannich reaction
Molecular Structure
natural products
Physical Sciences
Plants - chemistry
rearrangement
Science & Technology
total synthesis
IMINES
alkaloids
THIOL ESTERS
ALDEHYDES
natural products
Mannich reaction
HAPLOPHYTINE
FISCHER INDOLE SYNTHESIS
ASPIDOPHYTINE
total synthesis
ENANTIOSELECTIVE TOTAL-SYNTHESIS
rearrangement
CYCLIZATION
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Summary:Advancing alkaloid synthesis: (+)‐Haplophytine (see structure) was the target of a total synthesis featuring a highly stereoselective intramolecular Mannich reaction, Friedel–Crafts alkylation, oxidative rearrangement, and Fischer indole synthesis.
Bibliography:http://dx.doi.org/10.1002/anie.200902192
KAKENHI
ark:/67375/WNG-BZ1DQT95-Q
Grant-in-Aid for Scientific Research (B) - No. 20390003
istex:034AE9BA4DB63767C6F0CBE30D69AACC7A7C3CF7
This work was financially supported by the KAKENHI, a Grant-in-Aid for Scientific Research (B) (20390003), the Uehara Memorial Foundation, the Kato Memorial Bioscience Foundation, and the JSPS (predoctoral fellowship to H.U.).
Uehara Memorial Foundation
Kato Memorial Bioscience Foundation
JSPS
ArticleID:ANIE200902192
This work was financially supported by the KAKENHI, a Grant‐in‐Aid for Scientific Research (B) (20390003), the Uehara Memorial Foundation, the Kato Memorial Bioscience Foundation, and the JSPS (predoctoral fellowship to H.U.).
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902192