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Stereoselective hydroxylation of the 0-lactam ester 8 is a key step in a total synthesis of AI-77-B 1.The AI-77s are a small family of 3,4-dihydroisocoumarin derivatives isolated from a culture broth of Bacillus pumilus AI-77.1 AI-77-B 1 exhibits biological activity against stress ulcers in rats, yet is non-central suppressive, non-anticholinergic and non-antihistaminergic.2 Aspects of the chemistry and synthesis of AI-77-B have been studied,3-5 the first total synthesis having been described in 1989.6 AI-77-B is a dipeptide derived from the 3,4-dihydroisocoumarin 2 and the amino acid 3. Since the latter is a 0-amino acid, it was decided to investigate its synthesis from a homochiral (3-lactam, introducing the hydroxy substituents by cis-hydroxylation. (3-Lactams have recently been used in other (3-amino acid syntheses.7 We now report a total synthesis of AI-77-B using this approach.The (3-lactam aldehyde 4 is available in five steps from aspartic acid,g'9 and was condensed with methyl bis(2,2,2- '3 trifluoroethy1)phosphonoacetare 510 to give the (Z)-a,p-unsaturated ester 7. Oxidation using a catalytic amount of osmium tetroxide and N-methylmorpholine-N-oxide was found to be moderately stereoselective, and gave a mixture of diols 9 and 11, ratio ca. 80 : 20. The major diol was shown to be 0 0 CO2H

Chronic pelvic pain (CPP) is a frequent gynecologic complaint accounting for many diagnostic laparoscopies performed in general hospitals. Numerous organic conditions can cause CPP such as endometriosis and adhesions. However, studies assessing the prevalence of organic disease in women with CPP yield an extreme variation in results, suggesting the absence of any organic correlate in many patients with CPP. (See ref. 1 for a review.) On the other hand, a constantly high prevalence of psychopathology has been reported in patients with CPP, especially with respect to depressive mood, anxiety, and somatization. (See ref. 2 for a review.) Recent studies revealed an enhanced prevalence of chronic stress and traumatic life events, particularly sexual and physical abuse, in women with CPP.3-s In summary, these results suggest that CPP might be a stress-related syndrome.As stress is frequently associated with activation of the hypothalamic-pituitaryadrenal (HPA) axis, we recently explored psychoendocrinological features of women with CPP. Pain-free patients who underwent diagnostic laparoscopy because of infertility were recruited as controls. A high proportion of women with CPP had experienced sexual and/or physical abuse and fulfilled diagnostic criteria for posttraumatic stress disorder (PTSD) according to DSM-111-R criteria. Furthermore, women with CPP reported an enhanced total number of major life events, while these patients were typically not depressed. To assess HPA function, endocrine challenge tests were performed. In the corticotropin-releasing factor (0 stimulation test, women with