(±)-trans,cis-4-Hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one: synthesis and facile dimerization to decahydrodibenzofurans.
An efficient synthesis of (±)-trans,cis-4-hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one (3) has been developed from acetonide-protected meso-1,2-dihydrocatechol derivative 1 via photooxygenation, then Kornblum-DeLaMare rearrangement. The product is unstable unless its 4-hydroxy group is protected, as it undergoes facile dimerization in solution to a 1:1 mixture of diastereoisomeric decahydrodibenzofurans 8 and 9. A new synthesis of the dihydrocatechol 1 from 1,3-cyclohexadiene has also been developed.
Department of Chemistry, Imperial College, London, SW7 2AY, UK.
Victoria L
VL
Paddock
Robert J
RJ
Phipps
Almudena
A
Conde-Angulo
Araceli
A
Blanco-Martin
Carles
C
Giró-Mañas
Laetitia J
LJ
Martin
Andrew J P
AJ
White
Alan C
AC
Spivey
D001572:Benzofurans / Q000737:chemistry*; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001572:Benzofurans; D053138:Cyclohexenes; C558604:trans,cis-4-hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one