2000-2005

Publicação 15

“The Enantioselective Syntheses of Bisabolane Sesquiterpenes Lepistirone and Chaemonophyllon E”
Brocksom, T. J.; Zanotto, P. R.; Brocksom, U. Tetrahedron Lett2005, 46, 2397-2398.

DOI : 10.1016/j.tetlet.2005.02.058 

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Publicação 14

“The Enantioselective Syntheses of Bisabolane Sesquiterpenes Lepistirone and Chaemonophyllon E”

Brocksom, T. J.; Zanotto, P. R.; Brocksom, U. Tetrahedron Lett2005, 46, 2397-2398.

DOI : 10.1590 S0100-40422005000400024

Abstract :

The olefin metathesis reaction allows the exchange of complex alkyl units between two olefins, with the formation of a new olefinic link and a sub-product olefin usually ethylene. This reaction has found extensive application in the last ten years with the development of the Grubbs and Schrock catalysts, in total synthesis of complex organic molecules, as opposed to the very important use in the petrochemical industry with relatively simple molecules. This review intends to trace a historical and mechanistic pathway from industry to academy, before illustrating the more recent advances.

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Publicação 13

“Enantiopure Cycloheptenones from (R)-(-)-Carvone: Intermediates for Perhydroazulene Terpenoids”

Brocksom, T. J.; Brocksom, U.; de Sousa, D. P.; Frederico, D. Tetrahedron: Asymmetry 2005, 16. 3628-3632.

DOI : 10.1016/j.tetasy.2005.10.006

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Publicação 12

“Antinociceptive Profile of 2-Phenylselenenyl-1,8-Cineole in Mice”
De Sousa, D. P.; Raphael, E.; Brocksom, U.; Brocksom, T. J. Biol. Pharm. Bull2004, 27, 910-911.

Abstract

2-Phenylselenenyl-1,8-cineole (PSC) increased both the pentobarbital-induced sleeping time and the reaction time (up to 2 h) in the tail immersion method. PSC also caused dose-dependent inhibition of acetic acid induced writhing with maximum inhibition of 93.4% and was approximately 8.5-fold more potent than 1,8-cineole. These findings show that PSC presents sedative effect and significant antinociceptive activity.

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Publicação 11

“Synthesis of Guaiane Sesquiterpenoids by a Ring-Closing Metathesis Annulation Sequence”

Brocksom, T. J.; Brocksom, U.; Frederico, D. Tetrahedron Lett2004, 45, 9289-9291.

Doi : 10.1016/j.tetlet.2004.10.053

A new route for the synthesis of guaiane and nor-guaiane sesquiterpenoids is described, using a ring-closing metathesis annulation reaction sequence on a chiral enantiopure cycloheptenone derived from (R)-(−)-carvone.

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Publicação 10

“An Improved Three Step Synthesis of (-)-3?-Hydroxycarvone from (-)-Carvone”

Dos Santos, R. B.; Brocksom, T. J.; Zanotto, P. R.; Brocksom, U. Molecules2002, 7, 129-134.

DOI:10.3390/70200129

Abstract:

(-)-Carvone (3) has been efficiently transformed into (-)-3β-hydroxycarvone (1), which is expected to be a useful synthon or chiral template in the synthesis of natural molecules. This short and efficient synthesis of compound 1 involves regioselective and stereoselective α-hydroxylation of carvone via the trimethylsilyl-dienyl-ether derivative.

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Publicação 9

“Syntheses of Mintlactone and Isomintlactone”

Ferraz, H. M. C.; Longo Jr., L. S.; Grazini, M. V. A.; Brocksom, T. J.;. Brocksom, U. Synthesis ,2002, 2155-2164.

Doi: 10.1055/s-2002-34840

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Publicação 8

“First Comprehensive Bakkane Approach:? Stereoselective and Efficient Dichloroketene-Based Total Syntheses of (±)- and (-)-9-Acetoxyfukinanolide, (±)- and (+)-Bakkenolide A, (-)-Bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-Homogynolide A, (±)-Homogynolide B, and (±)-Palmosalide C”

Brocksom, T. J.; Coelho, F.; Deprés, J-P.; Greene, A. E.; de Lima, M. E. F.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc2002, 124, 15313-15325.

DOI: 10.1021/ja0208456

Abstract

Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol−aldol approach to low-energy aldol isomers.

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Publicação 7

“A Novel Dihydroxy Nor-Guaiane Sesquiterpene: Synthesis and Crystal Structure Analysis, Zukerman-Schpector”
J.; Caracelli, I.; Carvalho, C. C.; de Faria, M. L.; Silva, F. C.; Matias, L. G. de O.; Brocksom, T. J. J. Braz. Chem. Soc. 2001, 12, 154-158.

DOI : 10.1590/S0103-50532001000200005

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Publicação 6

“The Diels-Alder Reaction: an Update”

Brocksom, T. J.; Nakamura, J.; Ferreira, M. L.; Brocksom, U, J.Braz. Chem. Soc. 2001, 12, 597-622.

DOI: 10.1590/S0103-50532001000500004

Abstract

The last ten years have seen an explosive growth in synthetic applications of the Diels-Alder reaction, principally the intramolecular (IMDA) reaction but also the transannular (TADA) version. In this review we present these developments with special emphasis on the synthetic concepts and the experimental results and include related theoretical studies.

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Publicação 5

“A short synthesis of the monoterpenes (-)-6a-hydroxy- carvotanacetone and (-)-6ß-hydroxycarvotanacetone from (R)-(-)-carvone”

Dos Santos, R. B.; Zanotto, P. R.; Brocksom, T. J.; Brocksom, U. Flavour and Fragrance Journal 2001, 16, 303-305.

DOI : 10.1002/ffj.1001 

Abstract

6-Hydroxycarvotanacetone[2-methyl-5-(1-methylethyl)-6-hydroxycyclohex-2-en-1-one] has been isolated in small amounts from the essential oil of Laggera alata (D. Don) Sch. Bip. ex Oliv., although its absolute stereostructure has not yet been unequivocally established. A short synthesis of two diastereomers of 6-hydroxycarvotanacetone from (R)-(−)-carvone via regioselective epoxidation of its dienylsilyl ether is described. Copyright © 2001 John Wiley & Sons, Ltd.

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Publicação 4

“Diels-Alder Reactions in the Synthesis of Higher Terpenes, em “Organic Synthesis: Theory and Application”

Brocksom, T. J.; Corrêa, A. G.; Naves, R. M.; Silva Jr., F.; Catani, V.; Ceschi, M. A.; Zukerman-Schpector, J.; Toloi, A. P.; Ferreira, M. L.; Brocksom, U. ed. T. Hudlicky, JAI Press/Elsevier, vol. 5, 39-87, 2001.

ISBN: 0 08 044037 1

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Publicação 3

“Diels-Alder Reactions in the Synthesis of Higher Terpenes”, in: Organic Synthesis: Theory and Applications”

BROCKSOM, T. J. ed. T. Hudlick, JAI Press, Londres 2001, 39-87.

ISBN: 0-08-044037-1

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Publicação 2

“A Short Route to (-)-Mintlactone by Thallium(III)-Mediated Cyclization of (-)-Isopulegol”

Ferraz, H. M. C.; Grazini, M. V. A.; Ribeiro, C. M. R.; Brocksom, U.; Brocksom, T. J
J. Org. Chem. 2000, 65, 2606-2607.

DOI: 10.1021/jo991802j

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Publicação 1

“Enantiodivergent Syntheses of Cycloheptenone Intermediates for Guaiane Sesquiterpenes”

De Faria, M. L.; Magalhães, R. de A.; Silva, F. C.; Matias, L. G. de O.; Ceschi, M. A.; Brocksom, U. Brocksom, T. J.
Tetrahedron: Asymmetry 2000, 11, 4093-4103.

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