Abstract
Iodine-induced transannular ring enlargements of several epoxide derivatives of the cyclotrienol (Z,E,Z)-1-hydroxy-cyclododeca-2,5,9-triene ( 1) are presented. The diastereoselection exhibited by both the inter- and intramolecular reactions studied, appears to be associated with the conformational preferences of the macrocycle since simple molecular mechanics calculations allowed semiquantitative predictions in the product distributions. An absolute configurational study based on CD exciton chirality methodology is also included.
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