UNIQUE TRANS-SYN-CIS [6.6.7]-TRICYCLE DERIVATIVE FROM TRANSANNULAR DIELS-ALDER CONTRACTION OF A MODEL 15-MEMBERED TRANS-CIS-CIS MACROCYCLICTRIENE

Authors
DROUIN M HALL DG CAILLE AS DESLONGCHAMPS P
Citation
M. Drouin et al., UNIQUE TRANS-SYN-CIS [6.6.7]-TRICYCLE DERIVATIVE FROM TRANSANNULAR DIELS-ALDER CONTRACTION OF A MODEL 15-MEMBERED TRANS-CIS-CIS MACROCYCLICTRIENE, Acta crystallographica. Section C, Crystal structure communications, 53, 1997, pp. 1490-1493
Citations number
14
Categorie Soggetti
Crystallography
Journal title
Acta crystallographica. Section C, Crystal structure communications → ACNP
ISSN journal
01082701
Volume
53
Year of publication
1997
Part
10
Pages
1490 - 1493
Database
ISI
SICI code
0108-2701(1997)53:<1490:UT[DFT>2.0.ZU;2-O
Abstract
A model 15-membered trans-cis-cis macrocyclic triene, (trans-cis-cis)- tetramethyl (4E, 11Z,13E)-5-formylcyclopentadeca-4,11,1 3-triene-1,1,8 ,8-tetracarboxylate, C-24-H32O9, was synthesized and led to the exclus ive formation of a trans-syn-cis [6.6.7] tricyclic compound upon a tra nsannular Diels-Alder reaction. The structure of the precursor and a p -bromobenzoyl analog of the product, (trans-syn-cis)-tetramethyl rac-( 1S,2S,7R, 10R)-(8Z)-1-(4-bromobenzoyloxymethyl)tri 0.0(2,7)]pentadec-8 -ene-5,5,13,13-tetracarboxylate ethanol solvate, 3C(31)H(37)BrO(10).0. 76C(2)H(6)O, were determined in order to establish their exact geometr ies and ring-junction stereochemistries.