87681-25-2Relevant articles and documents
Intramolecular Diels-Alder reactions of silyl acetal trienes. The effect on stereoselectivity of allylic substitution
Craig,Reader
, p. 4073 - 4076 (1992)
The syntheses and thermal intramolecular Diels-Alder reactions of silyl acetal trienes possessing methyl groups at the allylic positions of the diene or dienophile are described. A model is proposed to account for the observed selectivities. The structure
Self-Assembly and Molecular Recognition in Water: Tubular Stacking and Guest-Templated Discrete Assembly of Water-Soluble, Shape-Persistent Macrocycles
Wang, Qiuhua,Zhong, Yulong,Miller, Daniel P.,Lu, Xiaoxing,Tang, Quan,Lu, Zhong-Lin,Zurek, Eva,Liu, Rui,Gong, Bing
supporting information, p. 2915 - 2924 (2020/02/04)
Supramolecular chemistry in aqueous media is an area with great fundamental and practical significance. To examine the role of multiple noncovalent interactions in controlled assembling and binding behavior in water, the self-association of five water-soluble hexakis(m-phenylene ethynylene) (m-PE) macrocycles, along with the molecular recognition behavior of the resultant assemblies, is investigated with UV-vis, fluorescence, CD, and NMR spectroscopy, mass spectrometry, and computational studies. In contrast to their different extents of self-aggregation in organic solvents, all five macrocycles remain aggregated in water at concentrations down to the micromolar (μM) range. CD spectroscopy reveals that 1-F6 and 1-H6, two macrocycles carrying chiral side chains and capable of H-bonded self-association, assemble into tubular stacks. The tubular stacks serve as supramolecular hosts in water, as exemplified by the interaction of macrocycles 1-H6 and 2-H6 and guests G1 through G4, each having a rod-like oligo(p-phenylene ethynylene) (p-PE) segment flanked by two hydrophilic chains. Fluorescence and 1H NMR spectroscopy revealed the formation of kinetically stable, discrete assemblies upon mixing 2-H6 and a guest. The binding stoichiometry, determined with fluorescence, 1H NMR, and ESI-MS, reveals that the discrete assemblies are novel pseudorotaxanes, each containing a pair of identical guest molecules encased by a tubular stack. The two guest molecules define the number of macrocyclic molecules that comprise the host, which curbs the "infinite" stack growth, resulting in a tubular stack with a cylindrical pore tailoring the length of the p-PE segment of the bound guests. Each complex is stabilized by the action of multiple noncovalent forces including aromatic stacking, side-chain H-bonding, and van der Waals interactions. Thus, the interplay of multiple noncovalent forces aligns the molecules of macrocycles 1 and 2 into tubular stacks with cylindrical inner pores that, upon binding rod-like guests, lead to tight, discrete, and well-ordered tubular assemblies that are unprecedented in water.
Total synthesis of (-)-pyrenophorol
Yadav, Jhillu S.,Reddy, Ganapuram Madhusudhan,Rao, Tenneti Srinivasa,Reddy, Basi V. Subba,Al Khazim Al Ghamdi, Ahmad
scheme or table, p. 783 - 787 (2012/04/10)
An efficient synthetic route has been developed for the synthesis of (-)-pyrenophorol employing Sharpless asymmetric epoxidation, olefin cross-metathesis, and intermolecular Mitsunobu cyclization. Georg Thieme Verlag Stuttgart · New York.
Synthesis of manzacidin A and C: Efficient construction of quaternary carbon stereocenters bearing nitrogen substituents
Ichikawa, Yoshiyasu,Okumura, Ken,Matsuda, Yasunori,Hasegawa, Tomoyuki,Nakamura, Mitsuhiro,Fujimoto, Aya,Masuda, Toshiya,Nakano, Keiji,Kotsuki, Hiyoshizo
experimental part, p. 614 - 622 (2012/02/05)
An efficient synthetic method for stereoselective construction of asymmetric quaternary carbon stereocenters, bearing nitrogen in the form of Boc-protected allyl amines, has been developed. This methodology is employed in the synthesis of marine alkaloids
