Chemistry
A regio- and stereo-selective annulation to form the 'inside-out' trans-bicyclo[9.2.1]tetradecane ring system
Document Type
Article
Abstract
Molecules from the family of trans-bicycles (commonly known as 'inside-out' bicycles) include numerous biologically active natural products as well as various structurally interesting synthetic challenges. The current results describe a synthetic strategy to access the trans-bicyclo[9.2.1]tetradecane ring system, which has been relatively unexplored until now. This method utilizes the inherent reactivity of trisubstituted cyclopentanones to control an intramolecular macrocyclization and establish the bicyclic structure as a single isomer. The cyclopentanone precursor is readily accessible as a single enantiomer, and the full synthetic sequence provides a 9% overall yield (85% average yield per step) of the bicycle.
Publication Title
Tetrahedron Letters
Publication Date
6-22-2016
Volume
57
Issue
25
First Page
2782
Last Page
2785
ISSN
0040-4039
DOI
10.1016/j.tetlet.2016.05.039
Keywords
Alkylation, macrocyclization, stereoselective synthesis, trans-bicycle
Repository Citation
Reardon, Michael B.; Yasgur, Brooke C.; and Jakobsche, Charles E., "A regio- and stereo-selective annulation to form the 'inside-out' trans-bicyclo[9.2.1]tetradecane ring system" (2016). Chemistry. 117.
https://commons.clarku.edu/chemistry/117
