000114965 001__ 114965
000114965 005__ 20190117191615.0
000114965 0247_ $$2doi$$a10.1021/ja076165q
000114965 037__ $$aARTICLE
000114965 245__ $$aTotal synthesis of (-)-pseudolaric Acid B
000114965 269__ $$a2007
000114965 260__ $$c2007
000114965 336__ $$aJournal Articles
000114965 500__ $$aDepartment of Chemistry, Stanford University, Stanford, California 94305-5080 0002-7863 FIELD Electronic Internat.Standard Doc. Number: United States Journal; Article; (JOURNAL ARTICLE) English
000114965 520__ $$aWe report the enantioselective synthesis of pseudolaric acid B (1a), a diterpene acid isolated from the bark of Pseudolarix kaempferi Gordon, which displays interesting antifungal, antifertility, and cytotoxic activity against multidrug resistant cell lines. Our synthesis utilizes a highly efficient metal-catalyzed [5 + 2] vinylcyclopropane- alkyne intramolecular cycloaddition to construct the polyhydroazulene core of the natural product. Elaboration to the tricyclic scaffold of the pseudolaric acids was completed with an intramolecular alkoxycarbonyl radical cyclization to form the quaternary center and a highly diastereoselective cerium acetylide addition to a methyl ketone for introduction of the acid side chain. [on SciFinder (R)]
000114965 700__ $$aTrost, Barry M.
000114965 700__ $$0243584$$aWaser, Jerome$$g181574
000114965 700__ $$aMeyer, Arndt
000114965 773__ $$j129$$k47$$q14556-7$$tJournal of the American Chemical Society
000114965 909C0 $$0252236$$pLCSO$$xU11811
000114965 909CO $$ooai:infoscience.tind.io:114965$$pSB$$particle
000114965 937__ $$aLCSO-ARTICLE-2007-001
000114965 970__ $$a0000000007/LCSO
000114965 973__ $$aOTHER$$rREVIEWED$$sPUBLISHED
000114965 980__ $$aARTICLE