Wilson, Carroll

Harkness MR, JB McDermott, DA Abramowicz, JJ Salvo, WP Flanagan, ML Stephens, FJ Mondello, RJ May, JH Lobos, KM Carroll, Ml Brennan, AA Bracco, KM Fish, GL Warner, PR Wilson, DK Dietrich,... 

Wilson J., Nobrega J., Carroll M. et al. Heterogenous subregional binding patterns of 3H-WIN 35,428 and 3H-GBR 12,935 are differentially regulated by chronic cocaine self-administration. J. Neurosci. 14 2966, 1994. 

Harkness MR, McDermott JB, Abramowicz DA, Salvo JJ, Flanagan WP, Stephens ML, Mondello FJ, May RJ, Lobos JH, Carroll KM, Brennan MJ, Bracco AA, Fish KM, Warner GL, Wilson PR, Dietrich DK, Lin DT, Morgan CB, Gately WL (1993) Science 259 503... 

The Carroll Rearrangement Synthesis of 5-Dodecen-2-one S. R. Wilson and C. E. Augelli, Department of Chemistry,... 

Goetz, C.G., Tanner, C.M., Wilson, R.S., Carroll, V.S., Como, P.G., and Shannon, K.M. (1987) Clonidine and Gilles de la Tourette syndrome double-blind study using objective rating method. Neurol 31 307—310. 

Zelena E, Dunn WB, Broadhurst D, Francis-Mclntyre S, Carroll KM, Begley P, O Hagan S, Knowles JD, Halsall A, Consortium H, Wilson ID, Kell DB (2009) Development of a robust and repeatable UPLC-MS method for the long-term metabolomic study of human serum. Anal Chem 81 1357-1364... 

Bondy PK Disorders of the adrenal cortex, in Wilson JD, Foster DW (eds) Textbook of Endocrinology. Saunders, New York, 1985, pp. 816-890. Carroll MC, Campbell RD, Porter RR Mapping of steroid 21-hydroxylase genes adjacent to complement component C4 genes in HLA, the major histocompatibility complex in man. Proc Natl AcadSci USA 82 521-525,1985. 

An improved version of the Carroll reaction, the ester enolate Carroll rearrangement, was reported in 1984 by Wilson and Ptice. Dianions of allylic acetoacetates, generated by treatment with 2 equiv. of LDA at -78 °C in THF, were rearranged at room temperature or 65 C to yield >keto acids in 40-80% yield (equation 12). In the course of a synthesis of the sesquiterpene isocomene, Snider and Beal used this method for the rearrangement of acetoacetate (73), prepared in 83% yield from reaction of cyclopen-tene (72) with diketene and a catalytic amount of DMAP (Scheme 11). The ( )-isomer of ketone (74) is obtained stereospecifically, since there is a severe steric interaction between the methyl groups in the Carroll rearrangement transition state leading to the (Z)-isomer. 

L. Lilge, C. O Carroll, B.C. Wilson (1997). A solubilization technique for photosensitizer quantification in ex vivo tissue samples. Journal of Photochem. and PhotobioL, B39, 229-235. 

Stephen R. Wilson and Corinne E. Augelll 210 THE CARROLL REARRANGEMENT 5-DODECEN-2-ONE... 

The cr-bonds in the cyclic phosphazenes, such as the hexa-chloro compound [PNClgls, are undoubtedly formed by or near-5p -hybrid orbitals of phosphorus, since the phosphorus atoms are four-co-ordinated and X-ray analysis indicates that they are probably tetrahedral. Wilson and Carrol suggest that the ring system is planar, whereas Liquori et conclude that the ring... 

More recent research has shown that the rate of the Carroll rearrangement is accelerated in the presence of a base. Wilson and Price reported that allylic aceto-acetates treated with 2eq. of lithium diisopropylamide (LDA) at -78 °C readily underwent the Carroll rearrangement to the desired fi-keto acids when warmed to 65 "C (Scheme 8.6) [6]. 

The Carroll rearrangement is often used as one of many key steps in the preparation of natural products due to its reliability as a stereodifferentiating reaction. Snider and Beal recently showed this in their formal synthesis of isocomene (41) (Scheme 8.17) [19]. Ketone 36 was reduced to alcohol 37 and treated with diketene to form the yS-keto ester 38. The [3,3]-sigmatropic Carroll rearrangement was performed using Wilson s procedure (2eq. of LDA, -78 to 65 °C) [6] to give the desired ketone 39 in 72% yield. This step was key in setting up the desired hindered carbon-carbon bond needed in the final product. An intramolecular cycloaddition and a few additional steps provided ketone 40, which is a late intermediate in Wenkert s isocomene (41) synthesis [20]. 

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