410531-68-9Relevant academic research and scientific papers
Stereoselective synthesis of medium-sized cyclic ethers: Application of C -glycosylation chemistry to seven- to nine-membered lactone-derived thioacetals and their sulfone counterparts
Suga, Yuto,Fuwa, Haruhiko,Sasaki, Makoto
, p. 1656 - 1682 (2014/03/21)
Stereoselective synthesis of α,α′-substituted medium-sized cyclic ethers has been achieved by means of nucleophilic substitution of the corresponding lactone-derived thioacetals and their sulfone counterparts. Nucleophilic substitution of medium-sized lactone-derived thioacetals could be achieved efficiently either by (i) activation with NIS/TMSOTf in the presence of allyltrimethylsilane or TMSCN or by (ii) oxidation to the corresponding sulfones followed by treatment with an appropriate organometallic species such as divinylzinc or dimethyl(2-phenylethynyl)aluminum. Interestingly, the stereochemical consequence was found to be largely dependent on the local structure of substrates. In some cases, the gauche steric interaction developed in the transition state was considered to be responsible for the observed diastereoselectivity. The present method enables an efficient synthesis of a variety of α,α′-substituted seven- to nine-membered cyclic ethers from readily accessible lactone precursors.
Convergent synthesis of the FGHI ring segment of yessotoxin
Kadota, Isao,Ueno, Hirokazu,Sato, Yuki,Yamamoto, Yoshinori
, p. 89 - 92 (2007/10/03)
A convergent synthesis of the FGHI ring segment of yessotoxin was achieved via the intramolecular allylation of an α-chloroacetoxy ether and subsequent ring-closing metathesis.
cis-3,4-dichlorocyclobutene as a versatile synthon in organic synthesis. Rapid entry into complex polycyclic systems with remarkably stereospecific reactions
Nicolaou,Vega,Vassilikogiannakis
, p. 4441 - 4445 (2007/10/03)
An efficient synthesis of cyclic polyether structures (e.g. 1), which are commonly found in natural products, can be realized from cis-3,4-dichlorocyclobutadiene (2). The versatility of synthon 2 and a mechanistic rationale for the regio- and stereospecif
