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Review
. 2015 Sep 9;115(17):8976-9027.
doi: 10.1021/cr500689b. Epub 2015 Apr 2.

Chemistry and Biology of Resveratrol-Derived Natural Products

Mitchell H Keylor  1 , Bryan S Matsuura  1 , Corey R J Stephenson  1
Affiliations
Review

Chemistry and Biology of Resveratrol-Derived Natural Products

Mitchell H Keylor et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Resveratrol (A) Biosynthesis and (B) Post-Synthetic Modification and Derivatization
Figure 1
Figure 1
Establishing the absolute configuration of (−)-ε-viniferin.
Figure 2
Figure 2
Numbering scheme for hopeaphenol.
Figure 3
Figure 3
Identification of α- and ε-viniferin, phytoalexin constituents of Vitis vinifera.
Figure 4
Figure 4
Reassignment of the structure of vaticaffinol.
Figure 5
Figure 5
Resveratrol oligomers with a dearomatized A2 resorcinol ring.
Scheme 2
Scheme 2. Atropisomerism of Shoreaketone and Its Acid-Mediated Interconversion to Isohopeaphenol Monomethyl Ether
Scheme 3
Scheme 3. Regioisomeric Modes of Resveratrol Dimerization
Scheme 4
Scheme 4. Proposed Biosynthesis of the 8–10′ Dimers
Scheme 5
Scheme 5. Niwa’s Brønsted-Acid-Mediated Conversion of ε-Viniferin to Various 8–10′ Dimers
Scheme 6
Scheme 6. Proposed Biogenic Relationship Between ε-Viniferin and the 8–10′ Dibenzocycloheptane Dimers
Scheme 7
Scheme 7. Proposed Biosynthesis of the 8–8′ Dimers
Scheme 8
Scheme 8. Oxidized Derivatives of 8–8′ Dimeric Natural Products
Scheme 9
Scheme 9. Whole Cell B. Cinerea-Mediated Dimerization of 1 to 8–8′ Dimers
Scheme 10
Scheme 10. 3–8′ Dimers are Commonly the Major Isomers Formed on Exposure of Resveratrol to Oxidants
Scheme 11
Scheme 11. Biosynthesis of Higher-Order Oligomers Is Convergent in Nature and Employs Both Radical and Polar Mechanisms
Scheme 12
Scheme 12. Pan’s Biosynthetic Reactions on the Formation of the 10–8′ Trimers
Scheme 13
Scheme 13. Divergent Biosynthesis of Regioisomeric 10–8′ and 8–10′ Trimers
Scheme 14
Scheme 14. Oxidized 8–10′ Trimers from Dipterocarpaceae
Scheme 15
Scheme 15. Proposed Biosynthesis of the 8–10′ Tetramers
Scheme 16
Scheme 16. Proposed Biosynthesis of the 8–8′ Trimers (A) and Tetramers (B)
Scheme 17
Scheme 17. Studies of the Biosynthesis of 8–8′ Trimers (A) and Tetramers (B)
Scheme 18
Scheme 18. Proposed Biogenesis of the 3–8′ Trimers and Tetramers
Scheme 19
Scheme 19. Pan’s Biogenic Studies of the Parthenocissins and Laetevirenols
Scheme 20
Scheme 20. Oligomerization by Intermolecular Trapping of Quinone Methide Intermediates
Scheme 21
Scheme 21. Biogenic Hypothesis for the Formation of Stemonoporol and Copalliferols A and B
Scheme 22
Scheme 22. Potential Role of Dirigent Proteins in the Stereoselective Coupling of Resveratrol
Scheme 23
Scheme 23. Sako’s Biomimetic Synthesis of Vitisin B
Scheme 24
Scheme 24. Oxidative Photocyclization of 7
Scheme 25
Scheme 25. Interconversion of Leachinol F/G to Parthenocissin A and Quadrangularin A
Scheme 26
Scheme 26. Hou Synthesis of Quadrangularin A
Scheme 27
Scheme 27. Li’s Synthesis of Protected Restrytisol Dimers and Interconversion to Pallidol
Scheme 28
Scheme 28. Total Synthesis of Quadrangularin A and Pallidol by Stephenson and Coworkers
Scheme 29
Scheme 29. Synthesis of Indane-Based Resveratrol Dimers from a Common Building Block
Scheme 30
Scheme 30. Electrophile-Promoted Interconversion of Indane Dimers to [3.2.1] and [3.3.0] Bicicyclooctanes
Scheme 31
Scheme 31. Synthesis and Structural Reassignment of Caraphenols B and C
Scheme 32
Scheme 32. Total Synthesis of Hopeanol and Hopeahainol A by Nicolaou and Chen
Scheme 33
Scheme 33. Preliminary Efforts Towards Dibenzocycloheptanones by Snyder and Coworkers
Scheme 34
Scheme 34. Synthesis of Heimiol A and Hopeahainol D by Snyder et al.
Scheme 35
Scheme 35. Synthesis of Hopeahainol A and Hopeanol by Snyder et al.
Scheme 36
Scheme 36. Chen’s Synthesis of Malibatol A and Shoreaphenol
Scheme 37
Scheme 37. Synthesis of Laetevirenol A by Heo et al.
Scheme 38
Scheme 38. Synthesis of Pauciflorol F by She and Pan
Scheme 39
Scheme 39. Mizoroki–Heck/Friedel–Crafts Sequence To Access Oxidized Forms of Resveratrol Dimers
Scheme 40
Scheme 40. Sarpong’s Synthesis of Pauciflorol F Using a Larock Annulation
Scheme 41
Scheme 41. Synthesis of Benzofuran-based Resveratrol Dimers Using C–H Activation
Scheme 42
Scheme 42. Synthesis of Diptoindonesin G using C–H Activation
Scheme 43
Scheme 43. Synthesis of Pauciflorol F Using a Nazarov/C–H Arylation Sequence
Scheme 44
Scheme 44. Synthesis of Resveratrol Dimers using a Decarboxylative Arylation/Oxidative Mizoroki–Heck Sequence
Scheme 45
Scheme 45. Asymmetric Synthesis of δ-Viniferin Using a Rh-Catalyzed C–H Insertion
Scheme 46
Scheme 46. Paradigm for the Synthesis of Higher-Order Oligomers through Iterative (A) Homologation and (B) Dihydrobenzofuran Synthesis
Scheme 47
Scheme 47. Synthesis of Higher-Order Oligomers Containing Bicyclo[3.3.0]octane Cores
Scheme 48
Scheme 48. Synthesis of Higher-Order Oligomers Containing Bicyclo[3.2.1]octane Cores
Scheme 49
Scheme 49. Total Synthesis of Vaticanol A Through in Situ Generation and Reactions of para-Quinone Methides
Scheme 50
Scheme 50. Total Synthesis of Caraphenol A by Snyder and Wright
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