Recent topics in total syntheses of natural dimeric naphthoquinone derivatives

  title={Recent topics in total syntheses of natural dimeric naphthoquinone derivatives},
  author={Shogo Kamo and Kouji Kuramochi and Kazunori Tsubaki},
  journal={Tetrahedron Letters},
8 Citations
Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone.
The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy  p -quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent
Enzymatic dimerization in the biosynthetic pathway of microbial natural products.
This review focuses on the enzymes involved in the dimerization in the biosynthetic pathway of microbial natural products, with an emphasis on cytochrome P450s, laccases, and intermolecular [4 + 2] cyclases, along with other atypical enzymes.
Structure-activity relationship studies on naphthoquinone analogs. The search for new herbicides based on natural products.
Strong inhibitory effects were observed for the isomeric forms 23 and 33 and the derivatives with a free hydroxyl group, i.e. 24 and 30, gave values higher than 70% inhibition for root length in barnyardgrass and perennial ryegrass.
Photocatalytic Homocoupling Transformations
Homocoupling reactions promoted by photocatalysts are not very abundant in the literature. However, the products generated from such processes are very interesting. In this review, we highlight the


Biomimetic syntheses of rubialatins A, B and related congeners.
The first total syntheses of rubialatins A and B, two newly discovered naphthohydroquinone dimers, were achieved with high efficiency and elegancy through rationally designed biomimetic approaches.
Biomimetic synthesis of zeylanone and zeylanone epoxide by dimerization of 2-methyl-1,4-naphthoquinone.
A biomimetic synthesis of zeylanone and Zeylanone epoxide has been accomplished starting from plumbagin, a natural monomeric naphthoquinone, followed by epoxidation of the resultant hydroquinone with molecular oxygen.
Three different dimerizations of 2-bromo-3-methyl-1,4-naphthoquinones.
Three types of dimeric naphthoquinones, which possess structurally diverse skeletons, can be prepared in one step from 2-bromo-3-methyl-1,4-naphthoppers, by a one-pot Stille-type reaction via vinylstannanes.
The highly strained hexacyclic framework of spiroxins, a family of 1,8-dihydroxynaphthalene-derived natural products, was efficiently constructed in ten steps from commercially available naphthalene-
Enantioselective Access to Bicyclo[3.2.1]octadienone Skeleton: Total Syntheses of (+)-Engelharquinone and Its Epoxide.
The first enantioselective total syntheses of engelharquinone (2) and its epoxide 3 have been achieved. The key steps include (1) catalytic asymmetric 1,4-addition of a naphthylboronic acid
Dimerisation of 2-alkyl-1,4-naphthoquinones in the presence of t-butylamine
Treatment of certain 2-alkyl-1,4-naphthoquinones with ethanolic t-butylamine resulted in dimerisation to give 12H-dibenzo[b,h]fluorene derivatives (II). Mixtures of these naphthoquinones gave low
Asymmetric 1,4‐Addition of Organoboron Reagents to Quinone Monoketals Catalyzed by a Chiral Diene/Rhodium Complex: A New Synthetic Route to Enantioenriched 2‐Aryltetralones
A novel synthetic approach to 2-aryltetralones with high ee has been developed through asymmetric 1,4-addition of arylboronic acids to naphthoquinone monoketals catalyzed by a rhodium complex with
Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization.
A viable method is reported for the synthesis of the bicyclo[3.2.1]octadienone scaffold in naturally occurring octaketide dimers. The procedure employs a reductive cyclization reaction mediated by an