Chemoenzymatic synthesis of the enantiomer of 4,12-Dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of stereum purpureum

Lan, PingBanwell, Martin G.Willis, Anthony C.2015-04-302015-04-301523-7060http://hdl.handle.net/1885/13353Compound ent-1 has been prepared by engaging a derivative of the enantiomerically enriched and microbially derived cis-1,2-dihydrocatechol 6 in an intramolecular Diels-Alder reaction, elaboration of the adduct so-formed to the cyclopentannulated bicyclo[2.2.2]octenone 3, and photochemical rearrangement of this to the cyclobutanone 2. By such means it has been established that 4,12-dihydroxysterpurene (1) is not the structure of the natural product isolated by Xie and co-workers from a culture broth of Stereum purpureum.We thank the Australian Research Council and the Institute of Advanced Studies for financial support. P.L. is the grateful recipient of a CSC Ph.D. Scholarship provided by the Government of the People’s Republic of China.© 2014 American Chemical Societyagaricalesbiological productscycloaddition reactionmolecular structurenuclear magnetic resonancesesquiterpenessorbusstereoisomerismbiomolecularChemoenzymatic synthesis of the enantiomer of 4,12-Dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of stereum purpureum201510.1021/ol50348172015-12-10