This review covers the chemical reactions, synthesis, and biological activities of tetracyclic diterpenoids including ent-kauranes, ent-beyeranes, ent-atisanes, ingenanes, tyglianes, stemodanes, stemaranes, sordarin, salvileucalin B, harringtonolide and hainanolidol. It comprises of the un-reviewed references from the year 2000.
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http://dx.doi.org/10.2174/1381612822666160105112218 | DOI Listing |
J Am Chem Soc
December 2024
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Euphorbialoid A () belongs to the rare diterpenoid family of premyrsinanes and exhibits potent anti-inflammatory effects. The 5/7/6/3-membered carbocycle (ABCD-ring) of contains 11 contiguous stereocenters and seven oxygen-containing functional groups. Moreover, four of the six hydroxy groups of are concentrated in the southern sector and flanked by four structurally different acyl groups.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province, 730000, China.
Kalmanol (1) is the first isolated kalmane-type grayanoid featuring a highly oxidized 5/8/5/5 tetracyclic carbon skeleton and 9 contiguous stereocenters. We have accomplished the efficient and asymmetric total synthesis of 1 in 16 steps from known compounds (20 steps from commercially available starting materials) by a modular synthetic strategy. A tetracyclic intermediate was prepared in a convergent manner through a Grignard reaction and a subsequent ring-closing metathesis reaction of two enantiomerically enriched fragments.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China.
A three-stage chemoenzymatic synthesis of the cyclopiane family and related diterpenes is reported. Deoxyconidiogenol with a 6/5/5/5-fused tetracyclic cyclopiane skeleton was first produced by an engineered E. coli host harboring the corresponding terpene cyclase PchDS.
View Article and Find Full Text PDFPlant Physiol Biochem
November 2024
Institute of Medicinal Plant Physiology and Ecology, School of Pharmaceutical Science, Guangzhou University of Chinese Medicine, Guangzhou, 510006, China. Electronic address:
Pogostemon cablin (Blanco) Benth (Patchouli) is an aromatic herb extensively used in pharmaceutical and cosmetic industries. Sesquiterpenes are the characteristic constitutes in patchouli which are synthesized in the glandular trichomes on leaves and stems. Gibberellic acid (GA), a tetracyclic diterpenoid, plays a crucial role in the formation of glandular trichome.
View Article and Find Full Text PDFMini Rev Med Chem
September 2024
Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Rokietnicka 3, 60- 806 Poznan, Poland.
Taxol is a compound with a rigid, tetracyclic structure of diterpene, which is characterized by significant antitumor properties. Firstly, Taxol has been isolated by extraction from the bark of the yew tree. However, the low level of availability obligated the researchers' world to uncover alternative techniques of Taxol obtainment.
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