10.1002/hlca.19900730606
In the research, chamigrene refers to a specific class of sesquiterpene compounds characterized by their unique structural features and chemical properties. Specifically, chamigrene-type sesquiterpenes are known for their presence in certain marine organisms, such as red seaweeds of the genus Laurencia, and are now found for the first time in a marine sponge, Spongia zimocca, in this study. The compound rogiolol acetate, isolated from the sponge, is described as a novel halogenated B-chamigrene-type sesquiterpene. This means it has a specific molecular framework typical of chamigrene compounds, including a spiro ring system and multiple halogen substituents (bromine and chlorine in this case). The study focuses on elucidating the detailed structure, configuration, and biogenetic pathway of rogiolol acetate, which represents a significant addition to the known diversity of chamigrene-type compounds in marine environments.
10.1021/jo00180a010
The research focuses on the total synthesis of (+)-aphidicolin and (+)-β-chamigrene, which are complex organic compounds belonging to the tetracyclic diterpene class. The purpose of the study was to develop an efficient synthetic process for these compounds, utilizing a series of chemical reactions including hetero-Diels-Alder condensation, Claisen rearrangement, and solvolytic α-route for the formation of the bicyclo[3.2.1]octane portion of the molecule. The synthesis involved a variety of chemicals such as α-methylene ketones, methyl methacrylate, quinoline, and various ester and ketone derivatives. The conclusions of the research highlighted the successful synthesis of the target compounds, with a particular focus on the rearrangement of intermediates to form the aphidicolane bicyclo[3.2.1]octane ring system, which was a central feature of the (+)-aphidicolin synthesis. The study also detailed the challenges encountered in the synthesis process, such as the introduction of the C16,C17 diol system and the stereochemical control of the hydroxylation of exo-olefinic ketone. The final product, (+)-aphidicolin, was confirmed to have the same physical and spectral properties as an authentic sample, validating the synthetic route developed in the study.