Factors influencing the Regioselectivity of Reactions involving Organocuprate Reagents and Allyl Acylates: Synthesis of Some Phenylthioprostanoids

Article abstract of DOI:10.1039/P19810001729

The lactone (4) reacted with the cuprate reagents (5) and (6) under standard conditions to give mainly the products (8) and (12) respectively derived from an S_N' anti-process.Under the same conditions the lactone (15) reacted with the cuprate reagents (5) and (6) through the S_N2 mode primarily to give as the major products the acids (23) and (19) respectively.The compounds (15), (19), and (23) were converted into the corresponding prostaglandin A₂ analogues (18), (22), and (26).