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Synthetic Studies on Dragmacidin D: Synthesis and Assembly of Three Fragments Towards an Advanced Intermediate
Author(s) -
Oikawa Masato,
Ikoma Minoru,
Sasaki Makoto
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100242
Subject(s) - sonogashira coupling , chemistry , natural product , combinatorial chemistry , yield (engineering) , total synthesis , modular design , stereochemistry , organic chemistry , palladium , catalysis , programming language , computer science , materials science , metallurgy
We report herein the approach to the key advanced intermediate in the synthesis of the bioactive marine natural product dragmacidin D. By employing a modular synthesis strategy of three fragments ( 5 , 7 , and 8 ), the advanced intermediate 3 has been successfully synthesized in 2.5 % yield over 15 steps by starting from nitrotoluene 20 . The synthesis also involves sequential cross‐coupling reactions, namely Sonogashira and Suzuki–Miyaura reactions, so that various analogues can be efficiently synthesized, which will allow the study of structure–activity relationships of dragmacidin D.