Terpenoids represent the largest family of natural products (NPs) with dramatically chemical and structural diversity, which makes terpenoids the important compound resources of drug discovery. However, comprehensive understanding on the structure− function features for terpenoid NPs is limited. In this work, we have systematically explored the chemical and biological space of terpenoid NPs, including their distribution, physicochemical properties, scaffold features, and functional applications, by utilizing various cheminformatics and bioinformatics approaches. We have not only confirmed that terpenoid NPs have good drug-likeness and great potential for drug discovery but, more importantly, illuminated the uniqueness of cyclic scaffold diversity in different species (plants, fungi, bacteria, and animals) and the specificity of biological function for the dominant fused-ring scaffolds of terpenoids. The present work supplies a valuable reference for identifying the new structure and unknown function of terpenoid NPs.
The asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone were achieved by using the Sharpless asymmetric epoxidation reaction to generate the stereogenic center and a ring-closing metathesis (RCM) for the formation of the lactone structure. Starting from 3-methyl-2-buten-1-ol, the asymmetric total synthesis was achieved in an efficient 6-step protocol with an overall yield of 16%.
Terpenes
Terpenes U 0200Total Synthesis of (±)-Isocembrene: A Tactic for Both Diene Construction and Macrocycle Formation. -A convergent and highly efficient strategy for the total synthesis of the title diterpenoid (IX) employing a Pd-catalyzed intramolecular Stille cross-coupling reaction as the key step is developed. -(ZHANG, F.; PENG, L.; ZHANG, T.; MEI, T.; LIU, H.; LI*, Y.; Synth.
C-C bond formation O 0282L-Proline Catalyzed Asymmetric Aldol Reactions of Protected Hydroxyacetone.-The L-proline catalyzed direct aldol reaction between Tbs-protected hydroxyacetone (I) with various aliphatic and aromatic aldehydes gives monoprotected 1,2 diols in good yields (40-90%) and with up to 95% e.e. With unsaturated aldehydes additionally a regioisomeric aldol product, in some cases even as main product, is obtained. -(LIU, H.; PENG, L.; ZHANG, T.; LI*, Y.; New J.
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