131614-91-0Relevant academic research and scientific papers
Partial racemization occurring in the hydroxylactonization of a δ,ε-Epoxy Amide
Enomoto, Masaru,Kuwahara, Shigefumi
, p. 2535 - 2537 (2013/01/09)
Acid-promoted hydroxylactonization of a δ,ε-epoxy amide took place via both 6-exo-tet and 7-endo-tet processes, causing a considerable degree of racemization of the resulting δ-hydroxyalkyl-δ-lactone.
The Development of Cyclic Sulfolanes as Novel and High-Affinity P2 Ligands for HIV-1 Protease Inhibitors
Ghosh, Arun K.,Lee, Hee Yoon,Thompson, Wayne J.,Culberson, Chris,Holloway, M. Katharine,et al.
, p. 1177 - 1188 (2007/10/02)
Design and synthesis of a novel series of protease inhibitors incorporating conformationally constrained cyclic ligands for the S2-substrate binding site of HIV-1 protease is described. We recently reported urethanes of 3-tetrahydrofuranyl as P2 ligands for HIV-1 protease inhibitors. Subsequently, we have found that the urethane of 3(S)-hydroxysulfolane further increased the in vitro potency of these inhibitors. Furthermore, introduction of a small 2-alkyl group cis to the 3-hydroxyl group of either heterocyclic system further enhanced enzyme affinity. The cis-2-isopropyl group thus far offered optimum enhancement of the inhibitory properties. This led to the discovery of inhibitor 43 (IC50 3.5 nM, CIC95 50+/-14 nM) of comparable in vitro antiviral potency to the current clinical candidate 1 (Ro 31-8959) but of reduced molecular weight due to the exclusion of the P3 quinoline ligand. Also, it has been demonstrated that the octahydropyrindene derivative 34 is an effective replacement of the P1' decahydroisoquinoline derivative.
LITHIATION OF BENZENE DERIVATIVES PROMOTED BY β-FUNCTIONALISED ALKYL GROUPS. ASYMMETRIC SYNTHESIS OF THE ISOCOUMARIN PORTION OF AI-77-B
Bertelli, Lucia,Fiaschi, Rita,Napolitano, Elio
, p. 669 - 672 (2007/10/02)
The title compound has been synthesized in five high-yielding steps from (2S,3R)-1,2-epoxy-5-methylhexan-1-ol, 12, prepared by Sharpless asymmetric epoxidation of allylic alcohols. The key step of the sequence was the clean metallation at position 2' of t
DIVERGENT ASYMMETRIC SYNTHESIS OF erythro- OR threo-3-AZIDO-1,2-EPOXIDES FROM THE SAME 2,3-EPOXY-1-ALKANOL. A CONVENIENT SYNTHESIS OF STATINE AND ITS 3-EPIMER
Bertelli, Lucia,Fiaschi, Rita,Napolitano, Elio
, p. 521 - 524 (2007/10/02)
A 2,3-epoxy-1-alkanol (obtained by Sharpless asymmetric epoxidation of the corresponding allylic alcohol), O-protected with a 2-methoxypropyl group, undergoes gighly regioselective oxirane ring opening by attack of azide ion at C-3 to afford a monoprotect
