Spiculoic Acids A and B, New Polyketides Isolated from the Caribbean Marine Sponge Plakortis angulospiculatus

Organic Letters

Volumn 6, Issue 1, 2004, Pages 75-78

  Huang, Xin Hui ^a   Van Soest, Rob ^b   Roberge, Michel ^a   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

POLYKETIDE; SPICULOIC ACID A; SPICULOIC ACID B; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; CYTOTOXICITY; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; SPECTROSCOPY; SPONGE (PORIFERA); STRUCTURE ANALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARBOXYLIC ACIDS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDANS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PORIFERA; STEREOISOMERISM;

EID: 0742269537     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0361047     Document Type: Article

References (17)

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3. For some examples, see: (a) Qureshi, A.; Stevenson, C. S.; Albert, C. L. ; Jacobs, R. S.; Faulkner, D. J. J. Nat. Prod. 1999, 62, 1205-1207. (b) Kobayashi, J.; Takeuchi, S.; Ishibashi, M.; Shigemori, H.; Sasaki, T. Tetrahedron Lett. 1992, 33, 2579-2580. (c) del Sol Jimenez, M.; Garzon, S. P.; Rodriguez, A. D. J. Nat. Prod. 2003, 66, 655-661. (d) Amira, R.; Afani, R.; Gravalos, L. G.; Akain, M.; Gaydou, E.; Vacelet, J. Kashman, Y. J. Nat. Prod. 2003, 66, 682-685. (e) Campagnuolo, C.; Fattorusso, C.; Fattorusso, E.; Ianaro, A.; Pisano, B.; Taglialatela-Scafati, O. Org. Lett. 2003, 5, 673-676. (f) Williams, D. E.; Allen, T. M.; van Soest, R.; Behrisch, H. W.; Andersen, R. J. J. Nat. Prod. 2001, 64, 281-285.
4. For some examples, see: (a) Qureshi, A.; Stevenson, C. S.; Albert, C. L. ; Jacobs, R. S.; Faulkner, D. J. J. Nat. Prod. 1999, 62, 1205-1207. (b) Kobayashi, J.; Takeuchi, S.; Ishibashi, M.; Shigemori, H.; Sasaki, T. Tetrahedron Lett. 1992, 33, 2579-2580. (c) del Sol Jimenez, M.; Garzon, S. P.; Rodriguez, A. D. J. Nat. Prod. 2003, 66, 655-661. (d) Amira, R.; Afani, R.; Gravalos, L. G.; Akain, M.; Gaydou, E.; Vacelet, J. Kashman, Y. J. Nat. Prod. 2003, 66, 682-685. (e) Campagnuolo, C.; Fattorusso, C.; Fattorusso, E.; Ianaro, A.; Pisano, B.; Taglialatela-Scafati, O. Org. Lett. 2003, 5, 673-676. (f) Williams, D. E.; Allen, T. M.; van Soest, R.; Behrisch, H. W.; Andersen, R. J. J. Nat. Prod. 2001, 64, 281-285.
5. For some examples, see: (a) Qureshi, A.; Stevenson, C. S.; Albert, C. L. ; Jacobs, R. S.; Faulkner, D. J. J. Nat. Prod. 1999, 62, 1205-1207. (b) Kobayashi, J.; Takeuchi, S.; Ishibashi, M.; Shigemori, H.; Sasaki, T. Tetrahedron Lett. 1992, 33, 2579-2580. (c) del Sol Jimenez, M.; Garzon, S. P.; Rodriguez, A. D. J. Nat. Prod. 2003, 66, 655-661. (d) Amira, R.; Afani, R.; Gravalos, L. G.; Akain, M.; Gaydou, E.; Vacelet, J. Kashman, Y. J. Nat. Prod. 2003, 66, 682-685. (e) Campagnuolo, C.; Fattorusso, C.; Fattorusso, E.; Ianaro, A.; Pisano, B.; Taglialatela-Scafati, O. Org. Lett. 2003, 5, 673-676. (f) Williams, D. E.; Allen, T. M.; van Soest, R.; Behrisch, H. W.; Andersen, R. J. J. Nat. Prod. 2001, 64, 281-285.
6. For some examples, see: (a) Qureshi, A.; Stevenson, C. S.; Albert, C. L. ; Jacobs, R. S.; Faulkner, D. J. J. Nat. Prod. 1999, 62, 1205-1207. (b) Kobayashi, J.; Takeuchi, S.; Ishibashi, M.; Shigemori, H.; Sasaki, T. Tetrahedron Lett. 1992, 33, 2579-2580. (c) del Sol Jimenez, M.; Garzon, S. P.; Rodriguez, A. D. J. Nat. Prod. 2003, 66, 655-661. (d) Amira, R.; Afani, R.; Gravalos, L. G.; Akain, M.; Gaydou, E.; Vacelet, J. Kashman, Y. J. Nat. Prod. 2003, 66, 682-685. (e) Campagnuolo, C.; Fattorusso, C.; Fattorusso, E.; Ianaro, A.; Pisano, B.; Taglialatela-Scafati, O. Org. Lett. 2003, 5, 673-676. (f) Williams, D. E.; Allen, T. M.; van Soest, R.; Behrisch, H. W.; Andersen, R. J. J. Nat. Prod. 2001, 64, 281-285.
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12. A voucher specimen (ZMAPOR 17511) has been deposited at the University of Amsterdam.
13. 3) for ester 4: δ 5.22, d, J = 2.4 Hz (H-3); 2.14, dd, J = 11.8, 11.4 Hz (H-5); 1.87, dq, J = 11.4, 6.5 (H-6); 2.38, ddd, J = 3.4, 5.0, 11.8 Hz (H-8); 2.62, dd, J = 11.8, 11.8 Hz (H-9); 1.60, m (H-10); 2.25, m (H-10′); 0.98, t, J = 7.3 Hz (H-11); 5.91, d, J = 16.0 Hz (H-13); 6.21, d, J = 16.0 Hz (H-14); 7.29, dd, J = 7.3, 1.9 Hz (H-16/20); 7.28, t, J = 7.3 Hz (H-17/19); 7.18, tt, J = 7.3, 1.9 Hz (H-18); 1.59, m (H-21); 1.70, m (H-21′); 0.82, t, J = 7.3 Hz (H-22); 2.25, m (H-23); 1.12, t, J = 7.3 Hz (H-24); 1.33, d, J = 6.5 Hz (H-25); 1.40, m (H-26); 1.74, m (H-26′); 0.65, t, J = 7.3 Hz (H-27); 3.70, s (OMe).
14. Kubanek, J.; Andersen, R. J. Tetrahedron Lett. 1997, 38, 6327-6330.
15. Auclair, K.; Sutherland, A.; Kennedy, J.; Witter, D. J.; Van den Heever, J. P.; Hutchinson, C. R.; Vederas, J. C. J. Am. Chem. Soc. 2000, 122, 11519-11520.
16. Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115.
17. A similar biogenesis, involving a different folding of a related linear polyketide intermediate and a final Diels Alderase catalyzed intramolecular [4 + 2] cycloaddition reaction, can lead to the plakotenins (see ref 1a,b).