Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone.
The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7.
Rustullet
Albert
A
Departament de Química, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain.
Alibés
Ramon
R
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism
D005663:Furans; C051061:oxetanocin; D000225:Adenine