Publications
552 results found
Jennings-White CLD, Holmes AB, Raithby PR, 1979, Diels-Alder reaction of furan and fumaryl chloride: X-ray crystal and molecular structure of an oxabicyclo[2.2.1]heptane derivative. Synthesis of reduction products of cis-maneonene-A, Journal of the Chemical Society, Chemical Communications, Pages: 542-544, ISSN: 0022-4936
The addition of fumaryl chloride to furan, followed by hydrolysis and bromolactonisation of the adduct, leads to the bromo-lactone acid (2a) which serves as a precursor for the synthesis of the reduction products (5a), (5b), and (6a) of cis-maneonene-A and of the tosylate (6b) whose X-ray crystal structure has been determined.
Mock GA, Holmes AB, Raphael RA, 1977, Spirocyclic synthesis by [4+2]-cycloaddition: the preparation of 11,13-dioxa-1,4-dithia-12, 12,18-trimethyl-10, 14, 17-trioxotrispiro[4.2.0.5.4.2]eicosane, Tetrahedron Letters, Vol: 18, Pages: 4539-4540, ISSN: 0040-4039
- Cite
- Citations: 17
Chaloner PA, Holmes AB, McKervey MA, et al., 1977, A synthetic approach to cyclo-octa-2,5,7-triene-1,4-dione, Journal of the Chemical Society, Perkin Transactions 1, Pages: 2524-2529, ISSN: 1472-7781
Cyclo-octa-2,5,7-triene-1,4-dione bisethylene acetal [(13) or (14)] has been prepared by bromination of cyclo-octane-1,4-dione bisethylene acetal (11) to give the tribromo-compound (12), and subsequent dehydrobromination. The dibromo-trans-cyclo-octene bisacetal (17) is an intermediate in the dehydrobromination reaction, but it was not possible to distinguish spectroscopically between structures (13) and (14) for the triene bisacetal. The triene bisacetal could not be converted into cyclo-octa-2,5,7-triene-1,4-dione (3).
Baxter AJG, Holmes AB, 1977, Synthetic studies in the piperidine alkaloid field. Part 1. The 2-azabicyclo[2.2.2]octan-5-one approach to prosopine, Journal of the Chemical Society, Perkin Transactions 1, Pages: 2343-2347, ISSN: 1472-7781
An approach to the synthesis of the Prosopis alkaloids utilising the Baeyer-Villiger reaction of methyl 2-benzyloxycarbonyl-5-oxo-2-azabicyclo[2.2.2] octane-3-carboxylate (6 ; R = CO2Me) is described. The boron trifluoride-ether catalysed cycloaddition to cyclohexadiene of methyl 2-(benzyloxycarbonylimino)acetate (8 ; R = CO2Me), generated in situ from methyl N-benzyloxycarbonyl-2-methoxyglycinate, gave a mixture of bicyclic adducts (9) and (10). Oxymercuriation of (9) gave the alcohol (11 ; R = H), and subsequent oxidation gave the ketone (6 ; R = CO2Me). Baeyer-Villiger oxidations of (6 ; R = CO2Me or CH2·O 2CPh) gave the lactones (14) and (15), respectively, and none of the desired lactone (7).
Chaloner PA, Holmes AB, 1976, The lithium enolate of cyclo-octa-2,4,6-trienone and its reactions with electrophiles, Journal of the Chemical Society, Perkin Transactions 1, Pages: 1838-1842, ISSN: 1472-7781
Lithium di-isopropylamide catalysed rearrangement of 7,8-epoxycyclo-octa-1,3,5-triene at low temperature gives the lithium enolate of cyclo-octa-2,4,6-trienone, which can be alkylated at C-8 with reactive electrophiles such as methyl iodide, allyl bromide, ethyl iodide, benzyl iodide, and benzeneselenenyl bromide. Bromination of the enolate also occurs at C-8, but reagents such as acetyl chloride and ethyl chloroformate yield only the products of O-acylation.
Holmes AB, Raphael RA, Wellard NK, 1976, Model studies in the histrionicotoxin series: a highly stereoselective synthesis of terminal cis enyne units., Tetrahedron Letters, Vol: 17, Pages: 1539-1542, ISSN: 0040-4039
- Cite
- Citations: 37
Chaloner PA, Holmes AB, McKervey MA, et al., 1975, Synthesis of cyclooctatriene-1,4-dione bisethyleneketal, Tetrahedron Letters, Vol: 16, Pages: 265-268, ISSN: 0040-4039
- Cite
- Citations: 5
Garratt PJ, Holmes AB, Sondheimer F, et al., 1973, Wittig reactions of 1,2-dihydro-1,2-bis(triphenylphosphoranylidene) benzocyclobutene. Synthesis of all-cis- and mono-trans-1,2,3,4,6,7,8,9- octahydrodibenzo[b,h]benzo[3,4]cyclobuta[1,2-e]thionin, analogues of biphenylene containing a thionin ring, Journal of the Chemical Society, Perkin Transactions 1, Pages: 2253-2256, ISSN: 1472-7781
A Wittig reaction between 1,2-dihydro-1,2-bis(triphenylphosphoranylidene) benzocyclobutene (5) and 2,2′-thiobiscyclohex-1-enecarbaldehyde (4) gave both all-cis- (7) and mono-trans- (8) 1,2,3,4,6,7,8,9-octahydrodibenzo[b,h] benzo[3,4]cyclobuta[1,2-e]thionin. Oxidation of the thionins with hydrogen peroxide gave the corresponding sulphoxides. In the case of the mono-trans-thionin (8), two isomeric sulphoxides were isolated, which differ only in the relative orientation of the oxygen atom and the trans-double bond. The barrier to ring inversion in these compounds must, therefore, be relatively high.
Holmes AB, Sondheimer F, 1971, Synthesis and valence isomerization of alkylated thia11annulenes, Journal of the Chemical Society D: Chemical Communications, Pages: 1434-1436, ISSN: 0577-6171
The synthesis of the alkylated mono-trans-thia11annulenes (4a) and (4b) is described, which readily undergo valence isomerization to the dihydrobenzothiepins (5a) and (5b).
Garratt PJ, Holmes AB, Sondheimer F, et al., 1971, The synthesis of mono-trans-dicyclohexenob,i-1,6-dithiacyclodeca-2,4,7,9- tetraene, a tetra-alkylated 1,6-dithia10annulene, Journal of the Chemical Society D: Chemical Communications, Pages: 947-948, ISSN: 0577-6171
The synthesis of mono-trans-dicyclohexeno-b,i-1,6-dithiacyclodeca-2,4,7,9- tetraene (5), a tetraalkylated 1,6-dithia10annulene, is described.
Holmes AB, Sondheimer F, 1970, The Synthesis of Fully Unsaturated 11-, 12-, and 13-Membered Sulfur Heterocycles, Journal of the American Chemical Society, Vol: 92, Pages: 5284-5285, ISSN: 0002-7863
- Cite
- Citations: 19
Garratt PJ, Holmes AB, Sondheimer F, et al., 1970, The Synthesis of Benzo[3,4]cyclobuta[1,2-e]dicyclohexeno[b,h]thionin, an Analog of Biphenylene Containing a Thionin Ring, Journal of the American Chemical Society, Vol: 92, Pages: 4492-4493, ISSN: 0002-7863
- Cite
- Citations: 25
This data is extracted from the Web of Science and reproduced under a licence from Thomson Reuters. You may not copy or re-distribute this data in whole or in part without the written consent of the Science business of Thomson Reuters.