TY - JOUR
T1 - Electrocyclic processes in aromatic biosynthesis
T2 - A biomimetic study of pseudorubrenoic acid A
AU - Rickards, Rodney W.
AU - Skropeta, Danielle
PY - 2002/5/6
Y1 - 2002/5/6
N2 - The possible involvement of 6π electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,11,13-tetraene (12a) to the cyclohexadiene 13 followed by dehydrogenation to the analogue 14 of the o-dialkyl-substituted aromatic metabolite pseudorubrenoic acid A (1).
AB - The possible involvement of 6π electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,11,13-tetraene (12a) to the cyclohexadiene 13 followed by dehydrogenation to the analogue 14 of the o-dialkyl-substituted aromatic metabolite pseudorubrenoic acid A (1).
KW - Biomimetic synthesis
KW - Biosynthesis
KW - Electrocyclase
KW - Electrocyclic reactions
KW - Pseudorubrenoic acid
UR - http://www.scopus.com/inward/record.url?scp=0037029829&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)00320-4
DO - 10.1016/S0040-4020(02)00320-4
M3 - Article
SN - 0040-4020
VL - 58
SP - 3793
EP - 3800
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -