Haterumadienone: A new puupehenone congener from an Okinawan marine sponge, Dysidea sp.

Chemistry Letters

Volumn 34, Issue 11, 2005, Pages 1530-1531

  Ueda, Katsuhiro ^a   Ueta, Tomoyuki ^a   Richard, Eric ^a   Siwu, Oktavianus ^b   Kita, Masaki ^b   Uemura, Daisuke ^a,b  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544461561     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1530     Document Type: Article

References (13)

1. The taxonomical assignment was performed by Prof. P. R. Bergquist, University of Auckland, New Zealand.
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3. a) P. Amade, L. Chevelot, H. P. Perzanowski, and P. J. Scheuer, Helv. Chim. Acta, 66, 1672 (1983).
4. b) M. T. Hamann and P. J. Scheuer, J. Org. Chem., 58, 6565 (1993).
5. c) S. S. Nasu, B. K. S. Yeung, M. T. Hamann, P. J. Scheuer, M. Kelly-Borges, and K. Coins, J. Org. Chem., 60, 7290 (1995).
6. d) M.-L. Bourguet-Kondracki, C. Debitus, and M. Guyot, Tetrahedron Lett., 37, 3861 (1996).
7. e) I. C. Pina, M. L. Sanders, and P. Crews, J. Nat. Prod., 66, 2 (2003).
8. 13C NMR data are given in Table 1.
9. 13C NMR data are given in Table 1.
10. 3, 125 MHz) δ 15.4 (q), 18.1 (t), 18.2 (t), 21.9 (q), 28.5 (q), 32.1 (q); 33.3 (s), 33.7 (q), 38.9 (t), 40.2 (t), 41.2 (s), 41.4 (t), 52.4 (t), 53.9 (d), 54.6 (d), 79.3 (s), 82.8 (s), 104.4 (d), 129.5 (s), 144.5 (d), 165.9 (s), 192.5 (s), 193.0 (s), 205.1 (s).
11. L. M. Jackman and S. Sternhell, "Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry," Pergamon Press, London (1969), p 271.
12. 3c another ring-contracted congener, is a diol that results from the cleavage of an ether bond in ring C.
13. Formation of the trione was observed by TLC and ESIMS upon treatment of the acetone adducts 3 and 4 with NaOH in aqueous MeOH. Although we tried to extract the sponge with EtOAc instead of acetone, we did not observe the presence of the trione itself. However, a more polar fraction, which was eluted with EtOAc-MeOH (9.5:0.5) in column chromatography, was treated with acetone to furnish the acetone adducts 3 and 4. Therefore, the trione hydrate 5 should be the major form in the equilibrium in the sponge extract.