Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins.

  title={Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins.},
  author={Christina Li Lin Chai and John A. Elix and Felicity K. E. Moore},
  journal={The Journal of organic chemistry},
  volume={71 3},
A concise formal total synthesis of the cytotoxic bisnaphthazarin derivative hybocarpone has been completed through the development of routes to the synthetic precursor, 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone. The oxidation of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6-methylnaphthalene under Rapoport conditions gave 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone in modest yields after basic hydrolysis. In addition, treatment of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6… 

Concerning the Stereoselectivity of the Oxidative Dimerization of 3-Alkyl-2-Hydroxy-1,4-Naphthoquinones in the Synthesis of Hybocarpone

Reinvestigation of 2-hydroxy-3-alkylnaphthoquinones oxidative dimerization was carried out. On the example of dihydrolapachol it is shown that the oxidative dimerization of

Total synthesis of (+)-neomarinone.

The first total synthesis of (+)-neomarinone has been achieved by following a concise and convergent route using methyl (R)-lactate and (R-3-methylcyclohexanone as chiral building blocks, which proves the relative and absolute stereochemistry of natural neomarin one.

Practical First Total Synthesis of the Potent Phytotoxic (±)‐Naphthotectone, Isolated from Tectona grandis

Naphthotectone is a quinone isolated recently from teak extracts of Tectona grandis. It has been shown to be one of the most abundant compounds and the most active compound isolated form teak. Thus,

Target ROS to induce apoptosis and cell cycle arrest by 5,7-dimethoxy-1,4-naphthoquinone derivative.

Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation.

The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene using a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner.

Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge Dysidea avara.

Dysidavarone A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o-vanillin. A highly

Palladium-catalyzed annulation of alkynes with ortho-halide-containing benzyl alcohols in aqueous medium.

The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate