TY - JOUR
T1 - Synthesis of the octahydroindole unit of aeruginosins via asymmetric hydrogenation of the Diels-Alder adducts of 2-amido-2,4-pentadienoate
AU - Hoshina, Yoichiro
AU - Doi, Takayuki
AU - Takahashi, Takashi
N1 - Funding Information:
This work was supported by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 14103013).
PY - 2007/12/17
Y1 - 2007/12/17
N2 - An optically active octahydroindole, the core unit of aeruginosins (Choi) was synthesized. The Diels-Alder reaction of Danishefsky's diene with methyl (Z)-2-acetamido-2,4-pentadienoates provided the adducts regioselectively in good yield. The adducts were converted to the l-Choi precursor by asymmetric hydrogenation, followed by acid cyclization.
AB - An optically active octahydroindole, the core unit of aeruginosins (Choi) was synthesized. The Diels-Alder reaction of Danishefsky's diene with methyl (Z)-2-acetamido-2,4-pentadienoates provided the adducts regioselectively in good yield. The adducts were converted to the l-Choi precursor by asymmetric hydrogenation, followed by acid cyclization.
UR - http://www.scopus.com/inward/record.url?scp=35748978556&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=35748978556&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.09.078
DO - 10.1016/j.tet.2007.09.078
M3 - Article
AN - SCOPUS:35748978556
VL - 63
SP - 12740
EP - 12746
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 51
ER -