Synthesis of Hydroxylated Bicyclic Amino Acids from L-tyrosine: Octahydro-1H-indole Carboxylates

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Sep 5

PMID 18767800

Citations 5

Authors

Joshua G Pierce

Dhanalakshmi Kasi

Makoto Fushimi

Anthony Cuzzupe

Peter Wipf

Affiliations

Soon will be listed here.

Abstract

A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed. The oxidative cyclization of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up.

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References

Kodani S, Ishida K, Murakami M . Aeruginosin 103-A, a thrombin inhibitor from the cyanobacterium Microcystis viridis. J Nat Prod. 1998; 61(8):1046-8. DOI: 10.1021/np980106w. View

Carroll A, Pierens G, Fechner G, de Almeida Leone P, Ngo A, Simpson M . Dysinosin A: a novel inhibitor of Factor VIIa and thrombin from a new genus and species of Australian sponge of the family Dysideidae. J Am Chem Soc. 2002; 124(45):13340-1. DOI: 10.1021/ja020814a. View

Hanessian S, Tremblay M, Petersen J . The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin. J Am Chem Soc. 2004; 126(19):6064-71. DOI: 10.1021/ja030669g. View

Le Bourdonnec B, Goodman A, Graczyk T, Belanger S, Seida P, DeHaven R . Synthesis and pharmacological evaluation of novel octahydro-1H-pyrido[1,2-a]pyrazine as mu-opioid receptor antagonists. J Med Chem. 2006; 49(25):7290-306. DOI: 10.1021/jm0604878. View

Ersmark K, Del Valle J, Hanessian S . Chemistry and biology of the aeruginosin family of serine protease inhibitors. Angew Chem Int Ed Engl. 2007; 47(7):1202-23. DOI: 10.1002/anie.200605219. View

Karanjule N, Markad S, Shinde V, Dhavale D . Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues. J Org Chem. 2006; 71(12):4667-70. DOI: 10.1021/jo0601617. View

Nie X, Wang G . Synthesis of a ring-oxygenated variant of the 2-carboxy-6-hydroxyoctahydroindole core of aeruginosin 298-A from glucose. J Org Chem. 2005; 70(22):8687-92. DOI: 10.1021/jo0507901. View

Hanessian S, Tremblay M . Tandem functionalization of nonactivated alkenes and alkynes in intramolecular N-acyloxyiminium ion carbocyclization. Synthesis of 6-substituted hydroindole 2-carboxylic acids. Org Lett. 2004; 6(25):4683-6. DOI: 10.1021/ol040053b. View

Wipf P, Spencer S . Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine. J Am Chem Soc. 2005; 127(1):225-35. DOI: 10.1021/ja044280k. View

10.

Doi T, Hoshina Y, Mogi H, Yamada Y, Takahashi T . Solid-phase combinatorial synthesis of aeruginosin derivatives and their biological evaluation. J Comb Chem. 2006; 8(4):571-82. DOI: 10.1021/cc0600270. View

11.

Valls N, Vallribera M, Carmeli S, Bonjoch J . Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic alpha-amino acid. Org Lett. 2003; 5(4):447-50. DOI: 10.1021/ol0273250. View

12.

Wipf P, Methot J . Total synthesis and stereochemical revision of (+)-aeruginosin 298-A. Org Lett. 2001; 2(26):4213-6. DOI: 10.1021/ol006759x. View

13.

Hanessian S, Ersmark K, Wang X, Del Valle J, Blomberg N, Xue Y . Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin. Bioorg Med Chem Lett. 2007; 17(12):3480-5. DOI: 10.1016/j.bmcl.2007.03.075. View

14.

Hanessian S, Margarita R, Hall A, Johnstone S, Tremblay M, Parlanti L . Total synthesis and structural confirmation of the marine natural product Dysinosin A: a novel inhibitor of thrombin and Factor VIIa. J Am Chem Soc. 2002; 124(45):13342-3. DOI: 10.1021/ja0208153. View

15.

Valls N, Vallribera M, Lopez-Canet M, Bonjoch J . Synthesis of microcin SF608. J Org Chem. 2002; 67(14):4945-50. DOI: 10.1021/jo025709y. View

16.

Fuertes M, Kaur J, Deb P, Cooperman B, Smith 3rd A . Design, synthesis, and evaluation of octahydropyranopyrrole-based inhibitors of mammalian ribonucleotide reductase. Bioorg Med Chem Lett. 2005; 15(23):5146-9. DOI: 10.1016/j.bmcl.2005.08.062. View

17.

Ohshima T, Gnanadesikan V, Shibuguchi T, Fukuta Y, Nemoto T, Shibasaki M . Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation. J Am Chem Soc. 2005; 125(37):11206-7. DOI: 10.1021/ja037290e. View

18.

Mmutlane E, Harris J, Padwa A . 1,3-dipolar cycloaddition chemistry for the preparation of novel indolizinone-based compounds. J Org Chem. 2005; 70(20):8055-63. DOI: 10.1021/jo0511492. View

19.

Valls N, Vallribera M, Bonjoch J . First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid. Chemistry. 2001; 7(16):3446-60. DOI: 10.1002/1521-3765(20010817)7:16<3446::aid-chem3446>3.0.co;2-0. View

20.

Hanessian S, Del Valle J, Xue Y, Blomberg N . Total synthesis and structural confirmation of chlorodysinosin A. J Am Chem Soc. 2006; 128(32):10491-5. DOI: 10.1021/ja0625834. View