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Abstract

Approach to the A-B Ring System of Forskolin through Biotransformation of Toluene

Cátedra de Química Orgánica, Facultad de Química, Gral. Flores 2124, Universidad de la República, Montevideo, Uruguay
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(3), 522-523; https://doi.org/10.3390/50300522
Published: 22 March 2000

Abstract

:
In the present work, we will intend to show that diol I, microbially derived from toluene using Pseudomonas putida 39D, is a suitable synthon for the synthesis of the A-B ring system of forskolin. The functionalization of diol I, to be used as ring-B, and the attempts of ring-A closure, will be disclosed.

Introduction

Chiral cyclohexadiendiols of the type of I, produced by microbial oxidation of arenes, have been extensively used as starting materials for the enantioselective synthesis of natural products. In this work, we present an approach to the synthesis of forskolin, based in a transfer of chirality from the homochiral diol I to the B ring of the diterpene, as shown in the retrosynthetic analysis.
Molecules 05 00522 i001

Experimental

We will present the optimization of the synthetic route to obtain a structure of type II, via oxidation reactions and selective protection-deprotection sequences of the hydroxyl groups. We will also present the synthetic approaches to an structure of type III which allows the ring A closure through an in- tramolecular Diels-Alder reaction. We will also discuss the attempts to close ring A using an intermo- lecular Diels-Alder cycloaddition, studying the viability of the reaction with different dienes and ex- perimental conditions.

Results and Discussion

We have synthesized enone IV, as a model to study the intramolecular Diels-Alder reaction. To date, results have shown serious difficulties in terms of reactivity and stability of the model molecule. That’s why we are trying different intermolecular cyclizations with molecules of type V, utilizing more reactive dienes.
Molecules 05 00522 i002

Acknowledgments:

CSIC, PEDECIBA, CONICYT.

References and Notes

  1. Gibson, D.; Hensley, M.; Mabry, T. Biochemistry 1970, 9, 1926.
  2. Hudlicky, T.; et al. Chem. Rev. 1996, 1195.
  3. Seoane, G.; Brovetto, M.; Schapiro, V.; Cavalli, G.; Sierra, A.; Padilla, P. New Journal of Chemistry 1999, 23, 549–556.

Share and Cite

MDPI and ACS Style

Schapiro, V.; Seoane, G.; García, G. Approach to the A-B Ring System of Forskolin through Biotransformation of Toluene. Molecules 2000, 5, 522-523. https://doi.org/10.3390/50300522

AMA Style

Schapiro V, Seoane G, García G. Approach to the A-B Ring System of Forskolin through Biotransformation of Toluene. Molecules. 2000; 5(3):522-523. https://doi.org/10.3390/50300522

Chicago/Turabian Style

Schapiro, V., G. Seoane, and G. García. 2000. "Approach to the A-B Ring System of Forskolin through Biotransformation of Toluene" Molecules 5, no. 3: 522-523. https://doi.org/10.3390/50300522

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