TY - JOUR
T1 - Chemoenzymatic total syntheses of ribisins A, B, and D, polyoxygenated benzofuran derivatives displaying NGF-potentiating properties
AU - Lan, Ping
AU - Banwell, Martin G.
AU - Willis, Anthony C.
PY - 2014/4/4
Y1 - 2014/4/4
N2 - Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
AB - Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
UR - http://www.scopus.com/inward/record.url?scp=84898067520&partnerID=8YFLogxK
U2 - 10.1021/jo500210k
DO - 10.1021/jo500210k
M3 - Article
SN - 0022-3263
VL - 79
SP - 2829
EP - 2842
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -