Universität zu Köln

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

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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:	Creators Email ORCID ORCID Put Code Loelsberg, Wibke UNSPECIFIED UNSPECIFIED UNSPECIFIED Werle, Susen UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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:	Keywords Language PSEUDOPTEROGORGIA-ELISABETHAE; ALLYLIC ALKYLATION; DITERPENE-GLYCOSIDES; GORGONIAN OCTOCORAL; CONJUGATE ADDITION; REVISION Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/47686