52431-65-9Relevant articles and documents
Regiospecific synthesis of bromojuglone derivatives
Heinzman, Stephen W.,Grunwell, John R.
, p. 4305 - 4308 (1980)
A large yield highly regiospecific one step procedure for the synthesis of 2- and 3-bromo-5-acetoxy-1,4-naphthoquinone has been achieved from the reaction between N-bromosuccin-imide and 1,5- and 1,8-diacetoxynaphthalene, respectively.
Naphthoquinone derivative or a salt thereof as an active ingredient and horticultural fungicide containing (by machine translation)
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Paragraph 0155, (2019/03/29)
[A] a naphthoquinone derivative or salt thereof, or a salt thereof as an active ingredient horticultural fungicide containing said derivative, and use thereof. [Solution] the ingredient, represented by the following formula. [In the formula, R1 And R2 Is, for example, are each independently a hydrogen atom, a halogen, amino, substituted C1 - C6 The alkylcarbonyloxy groups such as shown, however, R1 And R2 Is, not simultaneously hydrogen atoms, R3 Is, for example, C1 - C6 Alkyl, C3 - C8 Cycloalkyl, C1 - C6 Alkoxy groups, R5 R6 N - shown as, R4 Is, a hydrogen atom or a halogen atom, here, R5 And R6 The, each independently hydrogen atom or C1 - C6 The alkyl groups, R5 And R6 The, the nitrogen atom to which they are attached together, may form a hetero ring, however, R5 And R6 The, are not simultaneously hydrogen atoms. ][Drawing] no (by machine translation)
Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation
Nicolaou,Hale, Christopher R. H.,Nilewski, Christian,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Nilewski, Lizanne G.,Beabout, Kathryn,Wang, Tim T.,Shamoo, Yousif
supporting information, p. 12137 - 12160 (2014/11/08)
The details of the total synthesis of viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.
