(±)-<i>trans</i>,<i>cis</i>-4-Hydroxy-5,6-di-<i>O</i>-isopropylidenecyclohex-2-ene-1-one: Synthesis and Facile Dimerization to Decahydrodibenzofurans
Victoria L. Paddock
Robert J. Phipps
Almudena Conde-Angulo
Araceli Blanco-Martin
Carles Giró-Mañas
Laetitia J. Martin
Andrew J. P. White
Alan C. Spivey
10.1021/jo102314w.s003
https://acs.figshare.com/articles/journal_contribution/_i_trans_i_i_cis_i_4_Hydroxy_5_6_di_i_O_i_isopropylidenecyclohex_2_ene_1_one_Synthesis_and_Facile_Dimerization_to_Decahydrodibenzofurans/2686621
An efficient synthesis of (±)-<i>trans</i>,<i>cis</i>-4-hydroxy-5,6-di-<i>O</i>-isopropylidenecyclohex-2-ene-1-one (<b>3</b>) has been developed from acetonide-protected <i>meso</i>-1,2-dihydrocatechol derivative <b>1</b> 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 <b>8</b> and <b>9</b>. A new synthesis of the dihydrocatechol <b>1</b> from 1,3-cyclohexadiene has also been developed.
2011-03-04 00:00:00
Kornblum
mixture
cyclohexadiene
9.
synthesis
dimerization
photooxygenation
Facile Dimerization
diastereoisomeric decahydrodibenzofurans 8
tran
solution
dihydrocatechol 1
DecahydrodibenzofuransAn
rearrangement
meso
Synthesi
hydroxy