Chamigrane sesquiterpenes comprise a large class of secondary metabolites that have been isolated along with numerous lipids, alkaloids, and steroids from Rhodophyta, commonly known as red algae. Such sesquiterpenes continue to be isolated primarily from Laurencia, a genus of red algae, and are hypothesized to function as feeding deterrents against marine predators. Extensive studies describe the potential pharmacological properties of these metabolites and have reported significant antibacterial and antifungal bioactivities. The Laureaceteals are a subset of chamigrane sesquiterpenes that deviate from the skeletal structure of other natural products isolated from Laurencia, exhibiting an unusual tricyclic ring system. This project explores the total synthesis of a member of this family, Laureacetal C. Isolated from Laurencia nipponica in 1983, Laureacetal C is structurally interesting due to its novel spirocyclic acetal architecture. The structure accommodates a strained oxetane motif possessing three contiguous stereocenters and three neighboring fully substituted vicinal carbons. A synthesis of Laureacetal C has not been reported and the pharmacological properties of Laureacetal C are not well-documented. A concise total synthesis of this product is crucial as it will provide a sufficient quantity for biological testing. Synthetic efforts toward the total synthesis of the natural product Laureacetal C will be described. The chosen strategies allowed good yields, reproducibility, and scalability for several important intermediates.

Progress toward the total synthesis of laureacetal C

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