Structure and total synthesis of benzylthiocrellidone, a novel dimedone-based vinyl sulfide from the sponge Crella spinulata

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1999, Pages 847-848

  Lam, Hon Wai ^a,b   Cooke, Paul A ^a,b   Pattcndcn, Gerald ^a,b   Bandaranayake, Wickramasinghe M ^a,b   Wickramasinghe, Wasantha A ^a,b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b AUSTRALIAN INSTITUTE OF MARINE SCIENCE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006157206     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901323g     Document Type: Article

References (9)

1. W. M. Bandaranayake and W. A. Wickramasinghe, Australian Institute of Marine Science Report, 1995, No. 23 (27 pp.)-
2. For the dimedone-formaldehyde reaction see: (a) E. C. Horning and M. G. Horning, J. Org. Cliem., 1946, 11, 95. For an example of a naturally occurring prenylated cyclohexane-l,3-dione see: (ft) H. Obara, J. Onodera, Y. Machida and S. Yada, Bull. Client. Soc. Jpn., 1989, 62, 3034;
3. M. R. Cann, A. Davis and P. V. R. Shannon, J. Client. Soc., Perkin Trans, l, 1982, 375.
4. B. D. Akehurst and J. R. Bartels-Keith, J. Client. Soc., 1957,4798.
5. K. Fuchs and L. A. Paquette, J. Org. Clteni., 1994,59, 528.
6. (a) A. Z.-Q. Khan and J. Sandström, J. Client. Soc., Perkin Trans. ], 1988, 2085;
7. (b) D. Villemin and A. B. Alloum, Synthesis, 1991, 301. We produced 7 from dimedone using the literature procedure in an unoptimised 20% yield.
8. +) requires 413.1787.
9. 28O4S, Af = 412.52, monoclinic, a = 5.939(4), fc= 14.950(7), c= 11.748(7) A, j? = 91.14(6)°, U= 1042.9(11) A', T= 150(2) K, space group P2, (No. 4), Z = 2, flc= 1.314 g cnT3, /;(MoKa) = 0.183 mm"1, 3195 unique reflections measured and used in all calculations. Final fi,[2171 F £4a(F)] = 0.0988 and wR (all F2) was 0.244. CCDC reference number 207β12. See http://www.rsc.org/ suppdata/pl/1999/847 for crystallographic files in .cif format.