
TY  - JOUR
A1  - Banwell, Martin G. 
A1  - Clark, George R. 
A1  - Hockless, David C. R. 
A1  - Pallich, Susanne 
T1  - Model Studies Directed Towards the Synthesis of the Oxetane D-Ring of Paclitaxel: Assessment of the Oxyanion-Assisted Retro-Diels-Alder Reaction as a Means for Generating Oxete
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2002
VL  - 54
IS  - 11
SP  - 691
EP  - 704
KW  - 
UR  - https://doi.org/10.1071/CH01161 
N2  - In connection with attempts to generate oxete (8) via anionically assisted retro-Diels&#8211;Alder reaction, the oxetanes (11) and (12) have been prepared together with their acyclic analogues (35) and (36). The X-ray crystal structure of compound (11) has been determined. Each of the substrates (11), (12), (35) and (36) was treated with potassium hydride in the presence of 18-crown-6, conditions known to promote retro-Diels&#8211;Alder reactions in other systems. However, the first three substrates failed to engage in any such reaction even at temperatures up to 100&#x02DA;C. In contrast, at 18&#x02DA;C compound (36) reacted to give anthrone (13) in quantitative yield. These results indicate, inter alia, that regioelectronic effects play a crucial role in determining the success, or otherwise, of anionically-assisted retro-Diels&#8211;Alder reactions leading to polarized alkenes. 
ER  -

