학술논문
Synthetic Studies on Jadomycin Antiboitics / ジャドマイシン系抗生物質の合成研究
Document Type
Journal Article
Author
Source
Proceedings of the Symposium on Progress in Organic Reactions and Syntheses. 2008, :135
Subject
Language
Japanese
Abstract
Total synthesis of jadomycins, bioactive penta-cyclic isoquinoline alkaloids, was examined. Methyl 2-bromo-3-methoxy-5-methylbenzoate and 5-methoxy-1-tetralone was subjected to Pd coupling reaction followed by oxidation with osmium tetroxide to give a spirolactone as a key intermediate. Model reaction using methylamine after introduction of additional carbonyl function to effectively yield an 8H-benzo[b]phenanthridine skeleton through an aminonaphthoquinone. The use of methyl isoleucinate in place of methylamine as an amine source gave the corresponding aminonaphthoquinone in moderate yield.