1255920-99-0Relevant academic research and scientific papers
Synthesis of the C7-C23 fragment related to iriomoteolide-1a via B -alkyl suzuki-miyaura cross-coupling and indium-mediated aldehyde allylation
Liu, Yuanxin,Wang, Jian,Li, Huoming,Wu, Jinlong,Feng, Gaofeng,Dai, Wei-Min
scheme or table, p. 2184 - 2188 (2010/10/21)
Synthesis of the C7-C23 fragment and its 18R,19S-diastereomer of iriomoteolide-1a has been accomplished from the C7-C12 allyl bromide, the C13-C16 vinyl iodide, and the C17-C23 alkyl iodide fragments. These fragments were assembled first by the B-alkyl Suzuki-Miyaura cross-coupling to give the C13-C23 intermediate. The latter, after being transformed into the C13 aldehyde, was coupled to the C7-C12 allyl bromide in the presence of indium powder in THF-H2O (1:1) at 70deg;C to the fully functionalized C7-C23 fragment with orthogonal protecting groups at C19 (PMB ether), and C9, C14, and C22 (TBS, TES, and TBS ethers, respectively). Formation of the characteristic six-membered C9/C13-hemiacetal ring has been demonstrated after global desilylation using pyridine-buffered HF.
