Synthesis of Pyranonaphthoquinone Antibiotics Involving the Phthalide Annulation Strategy

Sven Claessens; Dashnie Naidoo; Dulcie Mulholland; Luc Verschaeve; Johannes van Staden; Norbert De Kimpe

doi:10.1055/s-2006-926248

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Synlett 2006(4): 0621-0623
DOI: 10.1055/s-2006-926248

LETTER

Synthesis of Pyranonaphthoquinone Antibiotics Involving the Phthalide Annulation Strategy

Sven Claessens^a, Dashnie Naidoo^b, Dulcie Mulholland^b, Luc Verschaeve^c, Johannes van Staden^d, Norbert De Kimpe*^a
^a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;
^b School of Chemistry, University of KwaZulu-Natal, Howard College Campus, 4041 Durban, South Africa
^c Department of Environmental Toxicology, Vito (Flemish Institute for Technological Research), Boeretang 200, 2400 Mol, Belgium
^d Research Centre for Plant Growth and Development, School of Botany and Zoology, University of Natal, Pietermaritzburg, Private Bag X01, Scottsville 3209, South Africa

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Publication History

Received 24 November 2005
Publication Date:
20 February 2006 (online)

Abstract
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Abstract

The synthesis of the pyranonaphthoquinone antibiotic pentalongin was performed using the phthalide annulation strategy. Annulation of the cyanophthalide onto 6H-pyran-3-one resulted in a hongconin analogue, which upon further elaboration was converted into the natural product.

Key words

annulations - natural products - quinones - phthalide - pentalongin

References and Notes

1 Thomson RH. Naturally Occurring Quinones 2nd ed.: Academic Press; London: 1971. p.282 ; see also p. 597

Google Scholar
2 Wang W. Li T. Milburn R. Yates J. Hinnant E. Luzzio MJ. Noble SA. Attardo G. Bioorg. Med. Chem. Lett. 1998, 8: 1579

Crossref Google Scholar
3a Hayashi T. Smith FT. Lee KH. J. Med. Chem. 1987, 30: 2005

Google Scholar
3b Lee H. Hong SH. Kim YH. Bioorg. Med. Chem. Lett. 1996, 8: 933

Google Scholar
4 Brimble MA. Nairn MR. Prabaharan H. Tetrahedron 2000, 56: 1937

Crossref Google Scholar
5 Naruta Y. Maruyama J. Recent Advances in the Synthesis of Quinonoid Compounds. The Chemistry of Quinonoid Compounds Vol. 2: Patai S. Rapoport Z. John Wiley; New York: 1988. p.241

Google Scholar
7a Hari L. De Buyck L. De Pooter HL. Phytochemistry 1991, 30: 1726

Crossref Google Scholar
7b De Kimpe N. Van Puyvelde L. Schripsema J. Erkelens C. Verpoorte R. Magn. Reson. Chem. 1993, 31: 329

Crossref Google Scholar
8 Kesteleyn B. Van Puyvelde L. De Kimpe N. J. Org. Chem. 1999, 64: 438

Crossref Google Scholar
9 Nguyen Van T. De Kimpe N. Tetrahedron Lett. 2004, 45: 3443

Crossref Google Scholar
10 Kesteleyn B. De Kimpe N. Van Puyvelde L. J. Org. Chem. 1999, 64: 1173

Crossref Google Scholar
11 Nguyen Van T. Kesteleyn B. De Kimpe N. Tetrahedron 2001, 57: 4213

Crossref Google Scholar
12 Nguyen Van T. De Kimpe N. Tetrahedron 2003, 59: 5941

Crossref Google Scholar
14 Pialat J.-P. Hoffmann P. Moulis C. Fouraste I. Labidalle S. Nat. Prod. Lett. 1998, 12: 23

Google Scholar
15 Kesteleyn B. De Kimpe N. Van Puyvelde L. Synthesis 1999, 1881

Article in Thieme Connect Google Scholar
16 Bulbule VJ. Koranne PS. Munot YS. Borate HB. Deshpande VH. Synth. Commun. 2003, 33: 587

Crossref Google Scholar
17 Kobayashi K. Uchida M. Uneda T. Tanmatsu M. Morikawa O. Konishi H. Tetrahedron Lett. 1998, 39: 7725

Crossref Google Scholar
18 Deshpande PP. Price KN. Baker DC. J. Org. Chem. 1996, 61: 455

Crossref PubMed Google Scholar
19 Cossy J. Taillier C. Bellosta V. Tetrahedron Lett. 2002, 43: 7263

Crossref Google Scholar
20 Eiden F. Wanner KT. Arch. Pharm. 1985, 548

Crossref Google Scholar
21a Kraus GA. Sugimoti H. Tetrahedron Lett. 1978, 2263

Google Scholar
21b Kraus GA. Cho H. Crowley S. Roth B. Sugimoto H. Prugh S. J. Org. Chem. 1983, 48: 3499

Google Scholar
22a Hauser FM. Mal D. J. Am. Chem. Soc. 1983, 105: 5688

Crossref Google Scholar
22b Hauser FM. Rhee RP. J. Org. Chem. 1978, 43: 178

Crossref Google Scholar
22c Hauser FM. Rhee RP. J. Am. Chem. Soc. 1979, 101: 1628

Crossref Google Scholar
23 Mitchell AS. Russell RA. Tetrahedron 1995, 51: 5207

Crossref Google Scholar
24a Gould SJ. Melville CR. Tetrahedron Lett. 1997, 38: 1473

Google Scholar
24b Cone MC. Melville CR. Gore MP. Gould SJ. J. Org. Chem. 1993, 58: 1058

Google Scholar
24c Pedersen JA. Spectrochim. Acta, Part A 2002, 52: 1257

Google Scholar
26 Giles RGF. Green IR. Taylor CP. Tetrahedron Lett. 1999, 40: 4871

Crossref Google Scholar

6

Van Puyvelde, L.; Hakizayezu, D.; Brioen, P.; De Kimpe, N.; De Vroey, C.; Bogaerts, J.; Hakizamungu, E., presented at International Congress on Natural Products Research, July 31 to August 4, 1994; Halifax, Canada, 1994.

13

De Kimpe, N.; Kesteleyn, B.; Nguyen, Van T.; Van Puyvelde, L. 18th International Congress of Heterocyclic Chemistry, July 29 to August 3, 2001; Yokohama, Japan, 2001, 120.

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5,10-Dimethoxy-1 H -benzo[ g ]isochromene-4-one ( 13): yellowish oil; ¹H NMR (acetone-d ₆): δ = 3.90 (3 H, s, OCH₃), 4.01 (3 H, s, OCH₃), 4.30 (2 H, s, CH₂C=O), 5.06 (2 H, s, CH₂O), 7.62 (1 H, ddd, J = 8.4, 7.0, 1.4 Hz, CH-7), 7.73 (1 H, ddd, J = 8.4, 7.0, 1.4 Hz, CH-8), 8.11 (1 H, dd, J = 8.4, 1.4 Hz, CH-9), 8.34 (1 H, dd, J = 8.4, 1.4 Hz, CH-6). ¹³C NMR (acetone-d ₆): δ = 62.13 (OCH₃), 63.14 (OCH₃), 64.46 (CH₂O), 74.50 (CH₂OC=O), 118.30 (C_quat), 122.01 (CH-9), 125.05 (CH-6), 126.84 (CH-7), 127.45 (C_quat), 129.08 (C_quat), 129.74 (CH-8), 131.74 (C_quat), 146.43 (C_quat), 155.64 (C_quat), 193.47 (C=O). IR (KBr): ν_max 1689 (C=O) cm^-1. MS (ES⁺): m/z = 258 [M⁺].

27

4-Hydroxy-3,4-dihydro-1 H -benzo[ g ]isochromene-5,10-dione ( 6): ¹H NMR (CDCl₃): δ = 3.86 (1 H, dd, J = 12.2, 3.8 Hz, CHCH _aH_b), 4.03 (1 H, dd, J = 12.2, 3.5 Hz, CHCH_a H _b), 4.49 (1 H, dd, J = 18.9, 1.65 Hz, OCH _aH_b), 4.76 (1 H, dd, J = 18.9, 0.6 Hz, OCH_a H _b), 4.82 (1 H, m, CHOH), 7.76 (2 H, m, CH₇-CH₈), 8.09 (2 H, m, CH₆-CH₉). ¹³C NMR (CDCl₃): δ = 60.18 (CH₂O), 63.23 (CHOH), 69.51 (CH₂), 126.38 (C-6 or C-9), 126.63 (C-9 or C-6), 131.83 (2 × C_quat), 134.28 (C-7 and C-8), 140.58 (C_quat), 143.74 (C_quat), 183.84 (C=O), 184.59 (C=O). IR (KBr): ν_max = 3468 (OH), 1661 (C=O) cm^-1. MS (ES⁺): m/z (%) = 231 (15) [M + H⁺], 213 (100) [M⁺ - H₂O].