Synthesis of (±)-Scopadulcic Acid B

Keywords

(±)-scopadulcic acid B - scopadulan diterpenoid - Grignard reaction - Brown hydroboration - Swern oxidation - divinylcyclopropyl rearrangement - Wittig reaction - tandem Heck cyclizations - directed ortho lithiation

Significance

Overman and co-workers reported the first total synthesis of (±)-scopadulcic acid B. The natural product showed activity as a strong inhibitor of H⁺ and K⁺-adenosine triphosphatases and thus becoming a potential lead agent for treatment of peptic ulcers.

Comment

After silyl ether formation, cyclopropane E underwent divinylcyclopropyl rearrangement to form cycloheptenone F which was further transformed to diene G. Treatment of the latter with catalytic Pd(OAc)₂ triggered the tandem Heck cyclizations yielding a mixture of H and I, which was subsequently oxidized to dienone J.

Publication History

Article published online:
28 January 2025