Cephalodiones A–D: Compound Characterization and Semisynthesis by [6+6] Cycloaddition
- 2 February 2021
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 60 (17), 9374-9378
- https://doi.org/10.1002/anie.202015332
Abstract
Cephalodiones A−D ( 1−4 ), the first example of C 19 ‐norditerpenoid dimers, were isolated and fully characterized from a Cephalotaxus plant. These new skeletal natural products shared a unique tricyclo[6.4.1.1 2,7 ]tetradeca‐3,5,9,11‐tetraene‐13,14‐dione core that was capped in the both ends with rigid multicyclic ring systems either C 2 ‐symmetrically or asymmetrically. Compounds 1−4 were proposed to be biosynthetically produced by the [6+6]‐cycloaddition of two identical C 19 ‐norditerpenoid troponoids, which was validated by the semisyntheses of dimers 2 − 4 . Moreover, some compounds showed significant inhibition on Th17 cell differentiation.Keywords
This publication has 45 references indexed in Scilit:
- Theionbrunonines A and B: Dimeric Vobasine Alkaloids Tethered by a Thioether Bridge from Mostuea brunonisOrganic Letters, 2018
- Appreciation of symmetry in natural product synthesisNatural Product Reports, 2017
- Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery and Biomimetic SynthesisOrganic Letters, 2016
- Structural Determination of (−)-SCH 64874 and Hirsutellomycin by SemisynthesisThe Journal of Organic Chemistry, 2016
- (+)- and (−)-Pestaloxazine A, a Pair of Antiviral Enantiomeric Alkaloid Dimers with a Symmetric Spiro[oxazinane-piperazinedione] Skeleton from Pestalotiopsis sp.Organic Letters, 2015
- A Macrocyclic Dimeric Diterpene with a C2 Symmetry AxisOrganic Letters, 2013
- Strategies for the synthesis of C2 symmetric natural products—a reviewTetrahedron, 2007
- Paradigms and paradoxes: Mechanisms for possible enhanced biological activity of bilaterally symmetrical chemicalsStructural Chemistry, 2006
- Epoxytwinol A, a novel unique angiogenesis inhibitor with C2 symmetry, produced by a fungusChemical Communications, 2005
- Molecular Bilateral Symmetry of Natural Products: Prediction of Selectivity of Dimeric Molecules by Density Functional Theory and Semiempirical CalculationsJournal of Natural Products, 2004