31469-16-6Relevant articles and documents
Total synthesis of (-)-rhizopodin
Dalby, Stephen M.,Goodwin-Tindall, Jake,Paterson, Ian
, p. 6517 - 6521 (2013)
Core assembly: The total synthesis of the myxobacterial metabolite rhizopodin, a potent actin-binding anticancer agent, has been achieved. The modular synthesis utilizes a common C1-C22 monomeric unit to assemble the dimeric 38-membered macrodiolide core, which was elaborated by a bidirectional boron-mediated aldol reaction to install the characteristic side-chains. The final global deprotection was critically dependent on the correct choice of silyl protecting groups at C16/C16′. Copyright
C?Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes
Wang, Ziyong,Wu, Jason,Lamine, Walid,Li, Bo,Sotiropoulos, Jean-Marc,Chrostowska, Anna,Miqueu, Karinne,Liu, Shih-Yuan
supporting information, p. 21231 - 21236 (2021/09/02)
A new family of carbon-bound boron enolates, generated by a kinetically controlled halogen exchange between chlorocatecholborane and silylketene acetals, is described. These C?boron enolates are demonstrated to activate 1,3-enyne substrates in the presence of a Pd0/Senphos ligand complex, resulting in the first examples of a carboboration reaction of an alkyne with enolate-equivalent nucleophiles. Highly substituted dienyl boron building blocks are produced in excellent site-, regio-, and diastereoselectivity by the described catalytic cis-carboboration reaction.
Gallium trihalide catalyzed sequential addition of two different carbon nucleophiles to esters by using silyl cyanide and ketene silyl acetals
Inamoto, Yoshihiro,Kaga, Yuta,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
supporting information, p. 11664 - 11668 (2014/10/15)
A sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β-cyano-β- siloxy esters. This is the first example of the sequential addition of two different carbon nucleophiles to esters. The employment of lactones provided α,α-disubstituted cyclic ethers with a cyano group and an ester moiety. A variety of esters and lactones are applicable to this reaction system.