Loelsberg, Wibke, Werle, Susen, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2012). An Enantioselective Total Synthesis of Helioporins C and E. Org. Lett., 14 (23). S. 5996 - 6000. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

Full text not available from this repository.

Abstract

A short and enantioselective total synthesis of helioporins C and E, which are bioactive marine diterpenes containing a serrulatane or amphilectane skeleton, was elaborated. The chirogenic step, i.e. a Cu(I)-catalyzed allylic alkylation of a cinnamyl chloride with methylmagnesium bromide, proceeded with virtually complete enantioselectivity (99% ee) in the presence of a chiral phosphine-phosphite ligand. The other stereocenters were diastereoselectively established through Me2AlCl-mediated cationic cyclization and Ir-catalyzed hydrogenation.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Loelsberg, WibkeUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Werle, SusenUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-476865
DOI: 10.1021/ol302898h
Journal or Publication Title: Org. Lett.
Volume: 14
Number: 23
Page Range: S. 5996 - 6000
Date: 2012
Publisher: AMER CHEMICAL SOC
Place of Publication: WASHINGTON
ISSN: 1523-7052
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PSEUDOPTEROGORGIA-ELISABETHAE; ALLYLIC ALKYLATION; DITERPENE-GLYCOSIDES; GORGONIAN OCTOCORAL; CONJUGATE ADDITION; REVISIONMultiple languages
Chemistry, OrganicMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/47686

Downloads

Downloads per month over past year

Altmetric

Export

Actions (login required)

View Item View Item