Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Science (Washington, DC, United States) called Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence, Author is Ma, Zhiqiang; Wang, Xiaolei; Wang, Xiao; Rodriguez, Rodrigo A.; Moore, Curtis E.; Gao, Shuanhu; Tan, Xianghui; Ma, Yuyong; Rheingold, Arnold L.; Baran, Phil S.; Chen, Chuo, which mentions a compound: 32780-06-6, SMILESS is O=C1O[C@H](CO)CC1, Molecular C5H8O3, Reference of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one.
Cycloaddition is an essential tool in chem. synthesis. Instead of using light or heat as a driving force, marine sponges promote cycloaddition with a more versatile but poorly understood mechanism in producing pyrrole-imidazole alkaloids sceptrin, massadine, and ageliferin. Through de novo synthesis of sceptrin and massadine, we show that sponges may use single-electron oxidation as a central mechanism to promote three different types of cycloaddition Addnl., we provide surprising evidence that, in contrast to previous reports, sceptrin, massadine, and ageliferin have mismatched chirality. Therefore, massadine cannot be an oxidative rearrangement product of sceptrin or ageliferin, as is commonly believed. Taken together, our results demonstrate unconventional chem. approaches to achieving cycloaddition reactions in synthesis and uncover enantiodivergence as a new biosynthetic paradigm for natural products.
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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI