✍ Scribed by Tony K.M Shing; Eric K.W Tam
No coin nor oath required. For personal study only.
The optically active crotepoxide 1 and iso-crotepoxide 2 have been constructed from quinic acid involving a singlet oxygen photooxygentation as the key step.
Recently, the chemotherapeutic potential of glycosidase inhibitors 1 as anti-HIV, 2 anti-metastasis, 3 and antihyperglycemic agents 4 has aroused considerable attention from the synthetic chemists. Crotepoxide 1, a cyclohexane oxide 5 isolated from the fruits of Croton macrostachys 6 and of Piperfutokadzura, 7 has been shown to display significant tumour-inhibitory activity against Lewis lung carcinoma in mice (LL) and Walker intramuscular carcinosarcoma in rats (VCM). 6a The structures of crotepoxide 1 and its diastereoisomer, isocrotepoxide 2, are related to those of (1R,6S)-cyclophellitol 3 and cyclophellitol 4, respectively. (1R,6S)cyclophellitol 38,3b and cyclophellitol 49 have been shown to be potent fl-D-and a-D-glucosidase inhibitors, respectively, presumably attributable to the structural resemblance with fl-D-and a-D-glucose. Along the same vein of reasoning, tumour inhibitor crotepoxide 1 might reveal C~-D-glucosidase inhibition and iso-crotepoxide 2 might inhibit fl-D-mannosidase. The presence of ester groupings in 1 and in 2 may be advantageous because the anti-HIV activity of tX-D-glucosidase inhibitors such as castanospermine and 1-deoxynojirimycin improved significantly by increasing the lipophilicity of the compounds via esterification of the hydroxy groups. 2b,10 zo_ A ° Ac ,, .
📜 SIMILAR VOLUMES
## Hoi o i i ( ' ~i i i ~p i ~i ~m ~s 20 (!Vm wpp/wneni S(,rics V d . 54). Springer. Berlin, 1979. [ I l l " H (160.5 Mtlr). 'H (500.1 MHr). and "P (122 M H d NMR data (CDCI,. 25 ('. rel,iti\c intensities i n parentheses): 6("8) = + 46.7(1). + 46.3(1). ('ii + 1 3 1 I, + l0.7(1). -3.1(1) (resonance