Factors influencing the regioselectivity of reactions involving organocuprate reagents and allyl acylates: synthesis of some phenylthioprostanoids
Abstract
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 SN′anti-process Under the same conditions the lactone (15) reacted with the cuprate reagents (5) and (6) through the SN2 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).