Synthetic Studies toward Aplysiasecosterol A: Concise Synthesis of the Tricyclic Core and Its Reactions for Introduction of the D Ring Fragment

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Abstract Aplysiasecosterol A, a 9,11-secosteroid, has a unique tricyclic γ-diketone skeleton including a hemiacetal. The concise and efficient synthesis of the tricyclic core was developed by using pseudo-desymmetrizing acetalization and acyl radical cyclization. Toward the total synthesis, an efficient method for the introduction of the D ring fragment was developed by using an organocuprate.