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Total Synthesis of Lavendamycin by a [2+2+2] Cycloaddition
Author(s) -
Nissen Felix,
Detert Heiner
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.201100131
Subject(s) - chemistry , cycloaddition , quinoline , nitrile , total synthesis , combinatorial chemistry , substrate (aquarium) , catalysis , organic chemistry , oceanography , geology
The total synthesis of the bacterial‐derived, pentacyclic, antitumor antibiotic lavendamycin has been achieved through a highly convergent strategy. The key step of this synthesis is a ruthenium‐catalyzed [2+2+2] cycloaddition of an electron‐deficient nitrile to an alkynyl‐ynamide to prepare the carboline scaffold. The elaborate cycloaddition substrate is obtained in few steps by an N ‐ethynylation using alkynyliodonium salt chemistry and two palladium‐catalyzed cross‐coupling reactions. An efficient synthesis of a halogenated quinoline‐5,8‐dione building block starting from hydroquinone is presented.