Download PDF
Synfacts 2014; 10(1): 0039
DOI: 10.1055/s-0033-1340395
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Tubular Structural Analogue of Helicene

Contributor(s):
Timothy Swager
,
Derik K. Frantz
Wixe T, Wallentin C.-J, Johnson MT, Fristrup P, Lidin S, Wärnmark K * Lund University, Sweden and Technical University of Denmark, Kongens Lyngby, Denmark
Synthesis of an Orthogonal Topological Analogue of Helicene.

Chem. Eur. J. 2013;
19: 14963-14969
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
 PDF Download Permissions and Reprints

Key words

helical structures - Friedländer condensation

Significance

Helical molecular systems, both natural and unnatural, continue to capture the interests of chemists. Using an enantiomerically pure bicyclic moiety to appropriately place kinks into the system, Wärnmark and co-workers report the synthesis of helical structure 1, an orthogonal topological analogue of helicene.


#

Comment

The synthesis of 1 is accomplished by repeated employment of a two-step set of reactions consisting of (1) ring-opening hydrolysis in acid and (2) Friedländer condensation with a chiral bicyclic ketone. By this strategy, monomer 2 is converted into ring-opened trimer 3, which is converted into trimeric ketone 4. Condensation of 4 and 3 affords the helical target 1.


#
#


   Permissions and Reprints