The Chemistry of Lauren-1-ene. VII. Further Rearrangements of Ring A Seco Derivatives

Abstract

Treatment of the keto ester (2a) with acid can lead to either the conjugated diene (3) or the non-conjugated diene (4a). The structure of (4a) has been deduced from chemical and spectroscopic studies and by X-ray analysis of the derived iodo ketone (10d). This series of decalin derivatives exhibits a thermodynamically stable cis ring junction. The factors which control the production of dienes (3) and (4a) have been elaborated. A rearrangement which leads to a new lactone (16a) is also described.