@article{oai:kanazawa-u.repo.nii.ac.jp:00014840, author = {Fujii, Tozo and Ohba, Masashi and Seto, Shigeki}, issue = {1}, journal = {Chemical & pharmaceutical bulletin}, month = {Jan}, note = {A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H2O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid.}, pages = {49--52}, title = {Quinolizidines. XXXIII. A chiral synthesis of (-)-ophiorrhizine, a pentacyclic quaternary indole alkaloid from ophiorrhiza major RIDL}, volume = {43}, year = {1995} }