Synthesis, Structure, and Antimalarial Activity of Some Enantiomerically Pure, cis??fused cyclopenteno??1, 2, 4??trioxanes

…, P Kamalaprija, J Mareda, G Bernardinelli…

Index: Jefford; Kohmoto; Jaggi; Timari; Rossier; Rudaz; Barbuzzi; Gerard; Burger; Kamalaprija; Mareda; Bernardinelli; Manzanares; Canfield; Fleck; Robinson; Peters Helvetica Chimica Acta, 1995 , vol. 78, # 3 p. 647 - 662

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Citation Number: 102

Abstract

Abstract Two pairs of enantiomerically pure cis-fused cyclopenteno-1, 2, 4-trioxanes (7, ent- 7 and 8, ent-8) are prepared (Schemes 1–3). Their identities are established by dye- sensitized photo-oxygenation of ent-7 and 8, ent-8 to the allylichydroperxides, reduction to the corresponding alcohols, and conversion to the (1S)-camphanates (Scheme 4), the structures of which are determined by X-ray analysis. The dynamic properties of ent-7 are ...