Current Organic Chemistry, Volume 7, No. 6, 2003
Contents
Enzymatic Peptide Synthesis: from the Substrate
Point of View Pp.515-554
Dar-Fu
Tai
The Chemistry of Epoxy Alcohols Pp.555-571
P.C.A.
Pena and S.M. Roberts
Sulfonate and Sulfonamide Activated Olefins
and Acetylenes in [4+2] Cycloaddition Reactions Pp.573-583
Albert
W.M. Lee, W.H. Chan, H.K. Zhang and P.F. Xia
1,3-Dipolar Cycloadditions in the Synthesis
of Carbohydrate Mimics. Part 2: Nitrones and Oximes Pp.100%-628
A.E.
Koumbis, J.K. Gallos
Abstracts
[Back to top] Enzymatic Peptide Synthesis: from the Substrate
Point of View
Dar-Fu
Tai
The focus of this review is to simplify the role of acyl donor (P1) and the nucleophile (Pī1) in an enzymatic reaction. The specificity of P1 and Pī1 is described and arranged in order. In this review, the relationship between the amino acid and enzyme is linked to facilitate the selection of an enzyme to catalyze the synthesis of the desired peptides.
[Back to top] The Chemistry of Epoxy Alcohols
P.C.A.
Pena and S.M. Roberts
Epoxy alcohols are extremely versatile building blocks in organic synthesis, due to their general availability in both enantiomeric series. The preferred methods for the subsequent stereoselective attack of various nucleophiles (hydride, carbon nucleophiles, nitrogen nucleophiles, oxygen nucleophiles, halogen ions, etc.) in a regioselective fashion at C2 and C3 are reviewed. The application of some of these methods in the synthesis of natural products and optically active compounds are described. Finally some reactions typical of homoallylic alcohols and their corresponding hydroxyepoxides are also reported.
[Back to top] Sulfonate and Sulfonamide Activated Olefins and Acetylenes in [4+2] Cycloaddition Reactions
Albert
W.M. Lee, W.H. Chan, H.K. Zhang and P.F. Xia
Sulfonate and sulfonamide are electron withdrawing activators for both vinyl and acetylenic units. These vinyl (acyclic and cyclic) and acetylenic sulfonates and sulfonamides are versatile dienophiles in inter- and intramolecular Diels–Alder reactions, as well as dipolarophiles in 1,3-dipolar cycloadditions. Asymmetric versions of these cycloaddition reactions are also known. Further manipulation of the cycloaddition products afforded interesting compounds that are useful synthons and building blocks in natural product synthesis and asymmetric synthesis.
[Back to top] 1,3-Dipolar Cycloadditions in the Synthesis
of Carbohydrate Mimics. Part 2: Nitrones and Oximes
This article (the second of three parts) reviews the use of 1,3-dipolar cycloaddition reactions of nitrones and the closely related oximes in the construction of carbohydrate mimics. Preparation of isoxazoline and carbocyclic nucleosides, isoxazoline fused systems, polyhydroxylated and aminopolyhydroxylated carbocycles and azasugars, amino sugars, polyhydroxylated alkaloids of the pyrrolidine and indolizidine series is described. It is organized depending on the dipole employed and subdivided into separate sections according to the inter- or intramolecular fashion applied and the nature of dipolarophiles and dipoles incorporated. It is mainly dedicated to the synthetic preparations and stereoselectivities observed with limited reports to biological tests and results.