Chemoenzymatic and Chemical Routes to the Nonproteinaceous Amino Acid Albizziine and Its Amide Derivative

Nina A. Dobrovinskaya; I. Archer; Alison N. Hulme

doi:10.1055/s-2008-1042756

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Synlett 2008(4): 513-516
DOI: 10.1055/s-2008-1042756

LETTER

Chemoenzymatic and Chemical Routes to the Nonproteinaceous Amino Acid Albizziine and Its Amide Derivative

Nina A. Dobrovinskaya^a, I. Archer^b, Alison N. Hulme*^a
^a School of Chemistry, The University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: Alison.Hulme@ed.ac.uk;
^b Ingenza Ltd., Wallace Building, Roslin BioCentre, Midlothian, EH25 9PP, UK

Further Information

Publication History

Received 14 November 2007
Publication Date:
12 February 2008 (online)

Abstract
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Abstract

A two-step route for the synthesis of albizziine from Nα-Boc-asparagine which proceeds in 65% overall yield is disclosed. A high-yielding, six-step route for the synthesis of its protected amido derivative gives rapid access to a key component of the complex aminopolyol natural product, zwittermicin A.

Key words

d-amino acid oxidase - Hoffmann rearrangement - amidation - urea formation

References and Notes

1 Gmelin R. Strauss G. Hasenmaier G. Z. Naturforsch., B: Chem. Sci. 1958, 13: 252

Google Scholar
2 Peiris PS. Seneviratne AS. Phytochemistry 1977, 16: 1821

Crossref Google Scholar
3 Evans SC. Burns PJ. Dutton M. Brown S. Phytochemistry 1990, 29: 2159

Crossref Google Scholar
4 He H. Silo-Suh LA. Handelsman J. Clardy J. Tetrahedron Lett. 1994, 35: 2499

Crossref Google Scholar
5 Evans CS. Clardy J. Hughes PE. Bell EA. Phytochemistry 1985, 24: 2273

Crossref Google Scholar
6a Brown EG. Turan Y. Phytochemistry 1996, 41: 1491

Crossref Google Scholar
6b Brown EG. Turan Y. Phytochemistry 1995, 40: 763

Crossref Google Scholar
7a Zhao C. Luo Y. Song C. Liu Z. Chen S. Yu Z. Sun M. Arch. Microbiol. 2007, 187: 313

Crossref Google Scholar
7b Chan YA. Boyne MT. Podevels AM. Klimowicz AK. Handelsman J. Kelleher NL. Thomas MG. Proc. Natl. Acad. Sci. U. S. A. 2006, 103: 14349

Crossref Google Scholar
7c Nair JR. Narasimman G. Sekar V. J. Appl. Microbiol. 2004, 97: 495

Crossref Google Scholar
8 Rogers EW. Molinski TF. Org. Lett. 2007, 9: 437

Crossref Google Scholar
9a Baldwin JE. Adlington RM. Birch DJ. J. Chem. Soc., Chem. Commun. 1985, 256

Google Scholar
9b Inouye S. Shomura T. Tsuruoka T. Ogawa Y. Watanabe H. Yoshida J. Niida T. Chem. Pharm. Bull. 1975, 23: 2669

Google Scholar
9c Kjaer A. Vesterager E. Acta Chem. Scand. 1960, 14: 961

Google Scholar
9d Rudinger J. Poduska K. Zaoral M. Collect. Czech. Chem. Commun. 1960, 25: 2022

Google Scholar
9e Kjaer A. Larsen PO. Acta Chem. Scand. 1959, 13: 1565

Google Scholar
10 Denis J.-N. Tchertchian S. Vallée Y. Synth. Commun. 1997, 27: 2345

Crossref Google Scholar
11 Drauz K. Kottenhahn M. Makryaleas K. Klenk H. Bernd M. Angew. Chem., Int. Ed. Engl. 1991, 30: 712

Crossref Google Scholar
12 For an improved synthesis, see: McKillop A. Taylor RJK. Watson RJ. Lewis N. Synthesis 1994, 31

Article in Thieme Connect Google Scholar
13 Trost E.-M. Fischer L. J. Mol. Catal. B: Enzym. 2002, 19-20: 189

Google Scholar
14 Fotheringham I. Archer I. Carr R. Speight R. Turner NJ. Biochem. Soc. Trans. 2006, 34: 287

Crossref Google Scholar
15 Chen C.-H. Koeppe RE. Biochim. Biophys. Acta 1970, 215: 184

Google Scholar
16 Work E. Biochim. Biophys. Acta 1955, 17: 410

Crossref Google Scholar
17 The enantiomeric excess was determined through precolumn derivatisation with o-phthalaldehyde (OPA) and N-isobutyryl-l-cysteine (IBC) and analysis on a conventional 5µ C-18 reverse-phase HPLC column, see: Brückner H. Westhauser T. Godel H. J. Chromatogr., A 1995, 711: 201

Crossref Google Scholar
18 Zhang L. Kauffman GS. Pasti JA. Yin J. J. Org. Chem. 1997, 62: 6918

Crossref Google Scholar
19 Taillades J. Boiteau L. Beuzelin I. Lagrille O. Biron J.-P. Vayaboury W. Vandenabeele-Trambouze O. Giani O. Commeyras A. J. Chem. Soc., Perkin Trans. 2 2001, 1247

Crossref Google Scholar
20a Nicolaou KC. Nevalainen M. Zak M. Bulat S. Bella M. Safina BS. Angew. Chem. Int. Ed. 2003, 42: 3418

Article in Thieme Connect Google Scholar
20b Schneider TL. Walsh CT. O’Connor SE. J. Am. Chem. Soc. 2002, 124: 11272

Article in Thieme Connect Google Scholar
20c Kawamoto I. Endo R. Ishikawa K. Kojima K. Miyauchi M. Nakayama E. Synlett 1995, 575

Article in Thieme Connect Google Scholar
21 Xia ZP. Smith CD. J. Org. Chem. 2001, 66: 3459

Crossref Google Scholar
22a Trotter NS. Brimble MA. Harris PWR. Callis DJ. Sieg F. Bioorg. Med. Chem. 2005, 13: 501

Crossref Google Scholar
22b MacDonald SJF. Clarke GDE. Dowle MD. Harrison LA. Hodgson ST. Inglis GGA. Johnson MR. Shah P. Upton RJ. Walls SB. J. Org. Chem. 1999, 64: 5166

Crossref Google Scholar
22c Pozdnev VF. Tetrahedron Lett. 1995, 36: 7115

Crossref Google Scholar
23 Khalafi-Nezhad A. Mokhtari B. Rad MNS. Tetrahedron Lett. 2003, 44: 7325

Crossref Google Scholar
24 Kunishima M. Kawachi C. Morita J. Terao K. Iwasaki F. Tani S. Tetrahedron 1999, 55: 13159

Crossref Google Scholar
25 Kunishima M. Kawachi C. Hioki K. Terao R. Tani S. Tetrahedron 2001, 57: 1551

Crossref Google Scholar
26 Gemma E. Hulme AN. Jahnke A. Jin L. Lyon M. Müller RM. Uhrín D. Chem. Commun. 2007, 2686

Crossref Google Scholar
27 Zhang Z. Van Aerschot A. Hendrix C. Busson R. David F. Sandra P. Herdewijn P. Tetrahedron 2000, 56: 2513

Crossref Google Scholar
29 Liu Q. Luedtke NW. Tor Y. Tetrahedron Lett. 2001, 42: 1445

Crossref Google Scholar

28

Boc deprotection using TFA, TFA-CH₂Cl₂, or HCl-dioxane, was found to be unsuccessful in this instance.