George F. Lundell

N-trimethylsilylpyrroles as dienes in the synthesis of 1,4-dihydronaphthalen-1,4-imines and isoindoles†

A convenient, general synthetic method for 1,4-dihydronaphthaIen-1,4-imines via the Diels-Alder addition of benzyne to N-trimethylsilylpyrrole is described. The N-trimethylsilyl protecting group protected the product from secondary benzyne reactions and was easily removed. The use of a 1,3-dipolar reagent to convert 1,4-dihydronaphthalen-1,4-imines to isoindoles via a retro-Diels-Alder sequence is illustrated.

Potent and Selective Oxytocin Antagonists Obtained by Chemical Modification of a Streptomyces Silvensis Derived Cyclic Hexapeptide and by Total Synthesis

Oxytocin (OT) is a neurohypophyseal hormone which has an important function in parturition.1 There is considerable evidence that the uterotonic action of OT and its stimulation of uterine prostaglandin release combine to initiate labor.2,3 Additionally, OT mediates the postpartum function of contracting the mammary myoepithelium to elicit milk letdown4 and has also recently been implicated as a key element in preterm labor.5,6 Attempts to further delineate these OT connected events have provided the impetus to discover agents which interact selectively and competitively at the OT receptor. Such compounds are invaluable in determining the physiological and pathophysiological role of OT and its close structurally related hormone, arginine vasopressin (AVP). Additional interest derives from the prospect of their use as novel therapeutic agents.