Geoffrey I. Feutrill

Thermal 1,5-rearrangement of a silyl group from oxygen to carbon

Abstract Trialkylsilyl ethers of 1,1-dioxygenated butadienes, substituted at position 3 by electron releasing substituents, undergo thermal rearrangement with 1,5-migration of the silyl group from oxygen to carbon.

1,4-anthraquinonoid dienophiles applicable to synthesis of linear tetracycles

Abstract Derivatives of 1,4-anthraquinones (3), (21) are shown to be good dienophiles for achieving strongly regiocontrolled synthesis of linear tetracycles, a property greatly enhanced by their ease of formation and of subsequent replacement of the chloride.

Stereochemistry and cycloaddition of 1,1,3-trioxy butadienes from β-keto esters

Abstract Spectroscopic analysis of the 1,1,3-trioxy dienes (1), (2) shows them to possess ( Z )-stereochemistry, contrary to several literature assignments; characterisation of derived cycloadducts and crystallographic analysis of one of them (20) establishes endo cycloaddition.

Synthesis of the naphthacenequinone SS-228R

Abstract The two structures (1) and (2) proposed for the naphthacenequinone SS-228R have both been synthesised, thereby establishing the correctness of structure (2).

Iridoids of garrya elliptica as plant growth inhibitors

Abstract Extracts from catkins of Garrya elliptica inhibit the growth of wheat embryos. The components responsible for this activity have been identified as the iridoids geniposide and geniposidic acid together with their aglucones.

Synthesis of a natural polychloro dinaphthofuran quinone

Abstract The hexachloro dinaphthofuran quinone (1), the only natural example of this ring system has been synthesised for the first time.

Dichloro quinones as dienophiles: synthesis of alizarin derivatives

Abstract 2,3-Dichloro quinonoid dienophiles react with 1,3-dioxy butadienes to give cycloadducts, which aromatise with uptake of external nucleophile to give 1,2-disubstitution in the newly formed aromatic ring. With oxy nucleophiles this has led to synthesis of natural alizarin derivatives.

Synthesis of bostrycoidin and 8-0-methylbostrycoidin

Abstract The antibiotic bostrycoidin (1) and its 8-0-methyl derivative (2), the only natural 2-azaanthraquinones, have been synthesized for the first time.

A new synthesis of the naphthopyran antibiotics

Abstract A known precursor (1) of the naphthopyran antibiotics has been synthesised from the napthoquinones (11) and (12) by reaction with the diene (5) and subsequent elaboration.

Regiochemistry of nucleophilic displacements in chloroquinones

Abstract Nucleophilic displacement of halide from 2-halo 1,4-quinones occurs at the ipso carbon or at the carbon vicinal to it depending on the nature of the nucleophile and the solvent.