Ethylene oxide (EtO), propylene oxide (PO) and epichlorohydrin (ECH) are important industrial chemicals widely used as intermediates for various synthetic products. EtO and PO are also environmental pollutants. In this review we summarize data published during the period 1990-2001 concerning both the genotoxic and carcinogenic effects of these epoxides in humans. The use of DNA and hemoglobin a...

The solid catalyst with high catalytic activity and enantioselectivity in the hydrolytic kinetic resolution (HKR) of epoxides was prepared by confining Co(Salen) in the nanocage of SBA-16 through reducing the pore entrance size using a silylation method. It was found that the activity of the solid catalysts increased with the number of [Co(Salen)] molecules per nanocage increasing, and the soli...

Pericosine E (6), a metabolite of Periconia byssoides OUPS-N133 was originally isolated from the sea hare Aplysia kurodai, which exists as an enantiomeric mixture in nature. The enantiospecific syntheses of both enantiomers of Periconia byssoides OUPS-N133 has been achieved, along with six stereoisomers, using a common simple synthetic strategy. For these efficient syntheses, highly regio- and ...

The title compound, C14H17NO4, features an epoxide-O atom fused to a pyrrolidyl ring, the latter having an envelope conformation with the N atom being the flap. The 4-meth-oxy-phenyl group is orthogonal to [dihedral angle = 85.02 (6)°] and lies to the opposite side of the five-membered ring to the epoxide O atom, while the N-bound ethyl ester group (r.m.s. deviation of the five fitted atoms = 0...

In this review, we describe the development by our research group of highly functionalized heterogeneous Olympic medal metal (gold, silver, and copper) nanoparticle catalysts using hydrotalcite as a support, aimed towards Green and Sustainable Chemistry. Olympic medal metal nanoparticles can cooperate with the basic sites on the hydrotalcite surface, providing unique and high performance cataly...

The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqua...

A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of β-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Δ22–23

Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, epoxide opening, rearrangements, metathesis and cyclopropanation. Applicatio...

Enantiomerically pure epoxides and vicinal diols are key chiral synthons. Epoxide hydrolases (EHs) offer access to both chiral epoxides and vicinal diols and the development of a cost-effective technology based on EHs offers a compelling ‘green’ alternative to current asymmetric chemical technologies. This article describes the assumptions, innovations and developments that have allowed Oxyrane...

Reaction of hexa-N-Boc neomycin B with TPP and DIAD in toluene results in the formation of an epoxide in ring IV, not an aziridine or azetidine as previously reported.