Total Synthesis of (+)-MPC1001B

The first total synthesis of an epidithiodiketopiperazine alkaloid, (+)‐MPC1001B, was accomplished. This synthesis features a tetra‐n‐butylammonium fluoride mediated intramolecular aldol reaction for forming the 15‐membered macrolactone ring, and the construction of an epidithiodiketopiperazine subs...

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Published inAngewandte Chemie Vol. 128; no. 1; pp. 291 - 295
Main Authors Kurogi, Taichi, Okaya, Shun, Fujiwara, Hideto, Okano, Kentaro, Tokuyama, Hidetoshi
Format Journal Article
LanguageEnglish
German
Published Weinheim WILEY-VCH Verlag 04.01.2016
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Aldehydes
Aldolreaktion
Alkaloide
Alkaloids
Chemical synthesis
Chemistry
Construction
Dithiodiketopiperazin
Fluorides
Forming
Makrolactone
Substructures
Synthesis
Synthesis (chemistry)
Totalsynthesen
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Summary:The first total synthesis of an epidithiodiketopiperazine alkaloid, (+)‐MPC1001B, was accomplished. This synthesis features a tetra‐n‐butylammonium fluoride mediated intramolecular aldol reaction for forming the 15‐membered macrolactone ring, and the construction of an epidithiodiketopiperazine substructure through a stepwise sulfenylation reaction involving a novel trityl trisulfide (TrSSS)‐group transfer. Strategische Ringschlüsse: Die erste Totalsynthese eines Epidithiodiketopiperazin‐Alkaloids, (+)‐MPC1001B, nutzt eine TBAF‐vermittelte intramolekulare Aldolreaktion zum Aufbau des 15‐gliedrigen Makrolactons und eine stufenweise Sulfenylierung für das Epidithiodiketopiperazin.
Bibliography:Cabinet Office, Government of Japan - No. LS008
istex:A89626F00FF33C0D3119CC6303D070A32DE25076
Grant-in aid for Scientific Research - No. 26253001; No. 25460003
ark:/67375/WNG-8NDWP4TR-J
ArticleID:ANGE201507830
JSPS
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201507830