Universität zu Köln

Hemmersbach, Lars and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2023). Studies Towards the Total Synthesis of Populusone: Stereoselective Construction of Functionalized 2-Oxa-bicyclo[2.2.2]octenes. Synlett, 34 (3). S. 238 - 243. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

A short and efficient synthetic access to functionalized compounds displaying major structural elements of the natural product populusone is elaborated by exploiting a diastereoselective Mukaiyama aldol addition followed by a triflic anhydride-induced oxa-Michael addition to construct the sensitive 2-oxa-bicyclo[2.2.2]octene unit as an enol triflate, which is directly used in a subsequent Suzuki cross -coupling. While attempts to close the strained 10-membered ring by means of Ru-catalyzed ring-closing metathesis were not successful, the developed synthetic scheme opens a rapid synthetic access to advanced intermediates, which may allow the completion of the total synthesis of populusone in the future.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Hemmersbach, Lars UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-658251
DOI:	10.1055/a-1983-1694
Journal or Publication Title:	Synlett
Volume:	34
Number:	3
Page Range:	S. 238 - 243
Date:	2023
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-2096
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language RING-CLOSING METATHESIS; HETERO-DIELS-ALDER; 10-MEMBERED RING; STEREOCHEMISTRY; SYSTEM Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/65825