Stereoselective Synthesis of the Pheromone (R)-(–)-Sulcatol, and Its Enantiopure (R)- and (S)-1-Mono-, -1,1-Di-, and -1,1,1-Trifluoro Analogues[1]

Arnone, Alberto; Bravo, Pierfrancesco; Panzeri, Walter; Viani, Fiorenza; Zanda, Matteo

doi:10.1002/(sici)1099-0690(199901)1999:1<117::aid-ejoc117>3.0.co;2-i

Cited by 13 publications

(4 citation statements)

References 43 publications

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“…Double bonds between the pyrrole rings in natural compounds are formed by successive treatment of a mixture of a sulfone and an aldehyde with DBU and PBu n 3 . 408 The reactions of a-sulfonyl anions 409,410 or anions of chiral sulfoxides 411 with carbonyl compounds were used for binding fragments through the CH 2 CO or CH 2 CH(OH) groups. Unsaturated sulfones were involved in cyclisation of acyclic g-hydroxyvinyl sulfones, 412 ± 414 metallation of vinyl sulfones at the C=C bond followed by the introduction of a substituent 415,416 and [4 + 2] cycloaddition of ethynyl sulfones to N-Boc-pyrrole.…”

Section: Nhmentioning

confidence: 99%

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Prilezhaeva¹

2000

Russ. Chem. Rev.

185

103

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A graphical treatment of the tone reproduction problem in television systems satisfactorily answered by extensive experimental work, using the techniques of subjective appraisal which have been increasingly developed in recent years. Direct comparison of a reproduction and an original, with all the parameters of the system accurately known, calls, of course, for a considerable experimental effort. Such limited observations as have been made, however, suggest that the shape of the curves at least gives a good impression of the relative effects of viewing cathode-ray tubes with different values of A, and operating under, different conditions. It is not intended to draw any conclusions or express any as to what form of reproduction characteristic is most desirable. There can, however, be little doubt that there are instances where faithful reproduction is not desirable -where, in fact, the television system can improve on the eye and convey the maximum of information or enhance the asthetic value of a scene by emphasizing certain luminosity differences at the expense of others. To a large extent the value of such distortions must be a matter of personal preference.What constitutes the most desirable form of characteristic is, again, a question which calls for large-scale experiment on a subjective basis; factors such as signal-to-noise ratio and the effect of the characteristic on apparent definition have to be taken into account.Reference may be made in passing to the results of Jones's investigation into the preferences of a large number of observers in the matter of photographic prints.Q) This investigation tends to show that preferred prints are those in which the gradient of the logL,/logL, curve is approximately unity for the medium tones, and that a greater fall in the gradient is acceptable towards black. It would be unwise to assume, however, that the results obtained are necessarily applicable to television practice, where the form of the transfer characteristics and the viewing conditions are different. One general principle which does not seem to be in dispute is that, whereas a considerable tolerance exists when the reproduction is in monochrome, colour calls for a much closer approach to fidelity in luminosity reproduction.Large-area luminance range in modern aluminized cathoderay tubes, in the absence of external light, appears to offer little scope for worth-while improvement. It is worth noting, however, that the importance of good detail luminance range in determining the subjective quality of television pictures has been stressed by Law@) and other writers.Assuming that an optimum characteristic, or range of characteristics, can be defined, practical realization of the optimum raises a number of issues, e.g. the relative contributions of the transmitting and receiving apparatus to the overall result, and whether the desired objective can best be arrived at by selection of the camera or cathode-ray tube characteristic or by suitable circuit design.It is hoped that the present communication may help...

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Section: Nhmentioning

confidence: 99%

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Prilezhaeva¹

2000

Russ. Chem. Rev.

185

103

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“…Sulcatol 5 is the male-produced aggregation pheromone, which was first isolated from Gnathotrichus Sulcatus . Its important biological activity for the insect pest control, together with its biochemical and chemical synthetic relation with another important pest attractant, pityol 6 , stimulated extensive interests in its enantioselective synthesis . By using our kinetic resolution, we successfully resolved the commercially available racemic alcohol in a single step, obtaining ( R )-sulcatol in 98% ee (Scheme ).…”

mentioning

confidence: 99%

Highly Efficient Chemical Kinetic Resolution of Bishomoallylic Alcohols: Synthesis of (R)-Sulcatol

Chen

Loh

2004

Org. Lett.

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“…Alternative approaches to the synthesis of this compound have been reported. [47][48][49][50] Several successful approaches to this kinetic resolution have been described in the literature applying such lipases as porcine pancreas lipase, [51][52][53][54] Candida antarctica lipase B 55 or Burkholderia cepacia lipase 56,57 (formerly Pseudomonas cepacia). A systematic investigation of the inuence of different solvents on the enantioselectivity of Burkholderia cepacia lipase in the kinetic resolution of (AE)-sulcatol was also described.…”

Section: Kinetic Resolution Of (Ae)-sulcatol Using Bcl As a Catalystmentioning

confidence: 99%

Increasing the activity and enantioselectivity of lipases by sol–gel immobilization: further advancements of practical interest

et al. 2014

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The entrapment of lipases in hydrophobic silicate matrices formed by sol-gel mediated hydrolysis of RSi(OCH3)3/Si(OCH3)4 as originally reported in 1996 has been improved over the years by a number of modifications. In the production of second-generation sol-gel lipase immobilizates, a variety of additives during the sol-gel process leads to increased activity and enhanced stereoselectivity in esterifying kinetic resolution. Recent advances in this type of lipase immobilization are reviewed here, in addition to new results regarding the sol-gel entrapment of the lipase from Burkholderia cepacia. It constitutes an excellent heterogeneous biocatalyst in the acylating kinetic resolution of two synthetically and industrially important chiral alcohols, rac-sulcatol and rac-trans-2-methoxycyclohexanol. The observation that the catalyst can be used 10 times in recycling experiments without losing its significant activity or enantioselectivity demonstrates the practical viability of the sol-gel approach.

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Stereoselective Synthesis of the Pheromone (R)-(–)-Sulcatol, and Its Enantiopure (R)- and (S)-1-Mono-, -1,1-Di-, and -1,1,1-Trifluoro Analogues[1]

Cited by 13 publications

References 43 publications

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Sulfones and sulfoxides in the total synthesis of biologically active natural compounds

Highly Efficient Chemical Kinetic Resolution of Bishomoallylic Alcohols: Synthesis of (R)-Sulcatol

Increasing the activity and enantioselectivity of lipases by sol–gel immobilization: further advancements of practical interest

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