Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers.

Syntheses of the enantiomers of malathion, malaoxon, and isomalathion are reported herein. Malathion enantiomers were prepared from (R)- or (S)-malic acid in three steps. Enantiomers of malathion were converted to the corresponding enantiomers of malaoxon in 52% yield by oxidation with monoperoxyphthalic acid, magnesium salt. The four isomalathion stereoisomers were prepared via two independent pathways using strychnine to resolve the asymmetric phosphorus moiety. The absolute configurations of the four stereoisomers of isomalathion were determined by X-ray crystallographic analysis of an alkaloid salt precursor. A high-performance liquid chromatography technique was developed to resolve the four stereoisomers of isomalathion, and to determine their stereoisomeric ratios.

A case of advanced borderline leprosy reevaluation of a case originally reported as lepromatous

This article concerns the reevaluation of the classification diagnosis of a Negro patient who had been diagnosed in Pittsburgh, Penna., in 1953 as lepromatous leprosy, which diagnosis had been accepted when he was admitted to the Federal Leprosarium at Carville, La. Actually, the condition was eather advanced borderline leprosy. The primary lesion on the right forearm had at first been thought by the´patient to be an insect bite, but it progressed and when biopsied six months later was reported to be "sarcoid" in nature, which presumably signifies "tuberculoid". When seen at the Aspinwall Veterans Administration Hospital after another eight months, it presented as a mother lesion of the aspect of a major tuberculoid lesion which had undergone borderline deterioration. On the face were many asymmetric small nodular and other lesions which evidently had arisen as an eruption in a tuberculoid reaction, but which had not - and never did - cause loss af the eyebrows. During the month of his first hospitalization there appeared a circinate lesion on the abdomen, described as similar to the one on the forearm. Histologically, the forearm lesion showed a complex picture with a predominance of lepromatous elements, containing an abundance of bacilli in most parts. In the deeper levels of the dermis the picture was definitely lepromatous, but in the main lesion mass in the upper levels the picture indicated that the basis had been a reactiobnal tuberculoid condition, although no distinct tuberculoid features remained. A significant feature of the principal biopsy specimen was the presence, in one end of the section, of a part of an "immune" area against which the active lesion ended abruptly. Such areas arise only by central healing of tuberculoid plaques, and never in lepromas. Although the patient left Carville against advice after only four months, to return to the Veterans Administration for outpatient treatment, his condition has cleared up. This favorable outcome is in accord with the relatively goood prognosis of borderline cases generally.