115268-43-4Relevant articles and documents
Macrocyclization via allyl transfer: Total synthesis of laulimalide [14]
Enev,Kaehlig,Mulzer
, p. 10764 - 10765 (2001)
-
Total synthesis of laulimalide: Assembly of the fragments and completion of the synthesis of the natural product and a potent analogue
Trost, Barry M.,Amans, Dominique,Seganish, W. Michael,Chung, Cheol K.
supporting information; experimental part, p. 2961 - 2971 (2012/04/23)
Herein, we present a full account of our efforts to couple the northern and the southern building blocks, the synthesis of which were described in the preceding paper, along with the modifications required to ultimately lead to a successful synthesis of laulimalide. Key highlights include an exceptionally efficient and atom-economical intramolecular ruthenium-catalyzed alkene-alkyne coupling to build the macrocycle, followed by a highly stereoselective 1,3-allylic isomerization promoted by a rhenium complex. Interestingly, the designed synthetic route also allowed us to prepare an analogue of the natural product that possesses significant cytotoxic activity. We also report a second generation route that provides a more concise synthesis of the natural product. All in one piece: Efforts to couple the northern and southern building blocks, synthesized in the preceding paper, along with modifications required to lead to a successful synthesis of laulimalide are discussed. Interestingly, the designed synthetic route also allowed the preparation of an analogue of the natural product that possesses significant cytotoxic activity (see scheme). A more concise, second-generation route to the natural product is also described. Copyright
Total synthesis of (-)-laulimalide: Pd-catalyzed stereospecific ring construction of the substituted 3,6-dihydro[2H]pyran units
Uenishi, Jun'Ichi,Ohmi, Masashi
, p. 2756 - 2760 (2007/10/03)
(Chemical Equation Presented) The potent anticancer agent (-)-laulimalide (1) was prepared through a versatile method that should allow access to other marine natural products. Key steps included a Pd-catalyzed 1,3 chirality transfer of an allylic alcohol
Synthesis and biological evaluation of (-)-laulimalide analogues
Gallagher Jr., Brian M.,Fang, Francis G.,Johannes, Charles W.,Pesant, Marc,Tremblay, Martin R.,Zhao, Hongjuan,Akasaka, Kozo,Li, Xiang-Yi,Liu, Junke,Littlefield, Bruce A.
, p. 575 - 579 (2007/10/03)
Analogues of the marine natural product (-)-laulimalide were prepared by total synthesis and evaluated in vitro for anticancer activity.