fused phenylcycloalkyl derivatives fused phenylcycloalkyl derivatives (rings with 3, 4, 7 or more members) Q 1040
-097Carbocyclic cis-(1.1.1)-Tris-σ-homobenzenes -Syntheses by Triple Epoxide → Cyclopropane Conversions, Structural Data, (. sigma.2s + σ2s + σ2s) Cycloreversions.-A weakly basic mixed cyanocuprate carbon nucleophile is the reagent of choice to open the triple epoxide (I) to fully substituted cyclohexane derivatives such as (II), which in several group manipulations can be transformed into cyclopropane derivatives such as (III). -(RUECKER, C.; MUELLER-BOETTICHER, H.; BRASCHWITZ, W.-D.; PRINZBACH, H.; REIFENSTAHL, U.; IRNGARTINGER, H.; Liebigs Ann./Recl. (1997) 5, 967-989; Inst. Org. Chem. Biochem., Albert-Ludwigs-Univ., D-79104 Freiburg/Br., Germany; EN)
Optimization and Scale-Up of an Asymmetric Route to the LTB 4 Inhibitor Ontazolast.-A potential industrial process involving a telescoped series of operations is described. Inexpensive chiral auxiliary α-pinene (I) is safely and effectively oxidized under phase transfer conditions to yield keto alcohol (II), the imine of which is alkylated with nearly complete chirality transfer. Auxiliary removal is followed by enantiomeric enrichment of key amine (VII) (90% e.e.) by transformation into its tartrate (¿99 e.e.), which is then directly converted into title compound ontazolast with 52% overall yield from (II). -(ROTH, G. P.; LANDI, J. J. JUN.; SALVAGNO, A. M.; MUELLER-BOETTICHER, H.; Org. Process Res.
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