New synthesis of (.+-.)-sirenin and a physiologically active analog

Harding, Kenn E.; Strickland, J. B.; Pommerville, Jeffrey C.

doi:10.1021/jo00255a045

Cited by 44 publications

(11 citation statements)

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“…7 Addition of dichloroketene to diene 15 took place with complete chemoand regiochemical control to provide 16. Similar reactions have been reported by Harding et al 8 Reductive removal of the chlorine atoms of 16 gave the ketone 17, which in turn afforded only lactone 18 by a Baeyer-Villiger reaction with peroxyacetic acid. Ozonolysis of the double bond of 18 led to a rather unstable compound 19, so aldol cyclization was carried out immediately with dilute HCl to give 20.…”

Section: Resultssupporting

confidence: 79%

Synthetic studies toward the kempane diterpenes. Dielsâ€“Alder additions to bicyclic dienes

Liu

Bao

Burnell

2001

J. Chem. Soc., Perkin Trans. 1

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Diels-Alder additions of 2,6-dimethyl-p-benzoquinone to the bicyclic dienes 24, 30 and 32 took place with very high regio-, stereo-and facial selectivity. Reduction and then alkylation of a tetracyclic adduct with 1,3-dithienium tetrafluoroborate provided compound 56, which has the correct stereochemistry at three key carbons for elaboration to the kempane diterpenes. Exploratory reactions with tricyclic model compounds and with tetracyclic adducts have been used to assess the development of the desired stereochemistry about the decalin moiety. X-Ray structures for 52, 53 and 59 were determined.Scheme 1 Initial retrosynthetic analysis. (Compound numbering in this Scheme follows that of the kempanes.)

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Section: Resultssupporting

confidence: 79%

Synthetic studies toward the kempane diterpenes. Dielsâ€“Alder additions to bicyclic dienes

Liu

Bao

Burnell

2001

J. Chem. Soc., Perkin Trans. 1

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“…In our case, only one of the two isomers has been isolated after acidic treatment of the crude mixture, diethylamine elimination only wcuring from 3a under these conditions. (4).-The mixture of adducts 3a and 3b (1 g, 4.4 mmoles) was impregnated on montmorillonite K-10 (3 g) and vigorously stirred in a Pyrex tube. The reaction mixture was irradiated in the focused MW reactor for 20 minutes at 100".…”

Section: Methodsmentioning

confidence: 99%

Improved and Expeditious Microwave Synthesis of Ethyl 1,3-Cyclohexadden-1-Carboxylate

Tesson

Deshayes

2000

Organic Preparations and Procedures International

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“…Their strategy relied on MacMillan’s asymmetric Diels–Alder reaction using imidazolidinone 390 as the catalyst 145. Accordingly, Diels–Alder reaction between diene 389 146 and acrolein in the presence of catalyst 390 afforded a 9:1 mixture of the desired endo adduct 391 and exo adduct 392 (Scheme ). Equilibration of both 391 and 392 with aq.…”

Section: Snider’s Synthesis Of (−)‐Nor‐platencin An Analogue Of Pmentioning

confidence: 99%

Discovery and Syntheses of “Superbug Challengers”—Platensimycin and Platencin

Palanichamy

Kaliappan

2010

Chemistry An Asian Journal

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Bacteria have developed resistance to almost all existing antibiotics known today and this has been a major issue over the last few decades. The search for a new class of antibiotics with a new mode of action to fight these multiply-drug-resistant strains, or "superbugs", allowed a team of scientists at Merck to discover two novel antibiotics, platensimycin and platencin using advanced screening strategies, as inhibitors of bacterial fatty acid biosynthesis, which is essential for the survival of bacteria. Though both these antibiotics are structurally related, they work by slightly different mechanisms and target different enzymes conserved in the bacterial fatty acid biosynthesis. This Focus Review summarizes the synthetic and biological aspects of these natural products and their analogues and congeners.

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New synthesis of (.+-.)-sirenin and a physiologically active analog

Cited by 44 publications

References 0 publications

Synthetic studies toward the kempane diterpenes. Dielsâ€“Alder additions to bicyclic dienes

Synthetic studies toward the kempane diterpenes. Dielsâ€“Alder additions to bicyclic dienes

Improved and Expeditious Microwave Synthesis of Ethyl 1,3-Cyclohexadden-1-Carboxylate

Discovery and Syntheses of “Superbug Challengers”—Platensimycin and Platencin

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