165105-99-7Relevant articles and documents
A formal synthesis of vinigrol
Poulin, Jason,Grise-Bard, Christiane M.,Barriault, Louis
, p. 2111 - 2114 (2012/04/10)
Two key reactions in a rapid assembly of the tricyclic core of vinigrol are a stereoselective Claisen rearrangement and an intramolecular Diels-Alder reaction. The method paves the way for a total synthesis of this synthetically challenging and biologically interesting natural product. Copyright
Oligospiroketals as novel molecular rods
Wessig, Pablo,Moellnitz, Kristian,Eiserbeck, Christiane
, p. 4859 - 4872 (2008/02/03)
A modular approach for the synthesis of molecular rods based on oligospiroketals has been developed. The strategy relies on different terminal and intermediate segments, which are joined by ketal formation between ketones and diols. For this purpose it was necessary to develop a new ketalization method to circumvent some problems related with the established methods. The terminal segments are either derived from 4-piperidinone or from 4-oxocyclohexane carboxylic acid whereas the intermediate segments rest on pentaerythritol and cyclohexane-1,4-dione. A series of trispiro (14-18), hexaspiro (19) and nonaspiro (20) compounds have been prepared and characterized. From these we realized that it is imperative to use solubility enhancing groups if more than seven rings are joined.
Enantioselective deprotonation of protected 4-hydroxycyclohexanones
Majewski, Marek,Mackinnon, John
, p. 1699 - 1704 (2007/10/02)
A series of derivatives of 4-hydroxycyclohexanone (1a-g) with the hydroxy group protected as a silyl ether (1a,b), ether (1d,g), an acetal (1c), or an ester (1e,f) were deprotonated with chiral, optically pure, lithium amides 3-9. The resulting non-racemic enolates were trapped as enol acetates. The enantioselectivity of deprotonation was up to 74percent ee.
