Convergent synthesis of the putative biogenetic precursor of mycaperoxide B and a norsesterterpene triene isolated from an Australian sponge

Synlett

Volumn , Issue 2, 1999, Pages 185-188

  Drew, M G B ^a   Harwood, L M ^a   Jahans, A ^a   Robertson, J ^a   Swallow, S ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

Chiral synthesis; Marine norsesterterpene; Mycaperoxide

Indexed keywords

ALKADIENE; NAPHTHALENE DERIVATIVE; PEROXIDE; TERPENE DERIVATIVE;

ARTICLE; AUSTRALIA; BIOSYNTHESIS; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRECURSOR; SPONGE (PORIFERA); STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032909973     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2580     Document Type: Article

References (30)

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15. For examples see: J. D. Ballantyne and P. J. Sykes, J. Chem. Soc. (C), 1970, 731; S. C. Welch, A. S. C. P. Rao, J. T. Lyon and J-M. Assercq, J. Am. Chem. Soc., 1983, 105, 252; W. M. Daniewski, E. Kubak and J. Jurczak, J. Org. Chem., 1985, 50, 3963; K. H Schulte-Elte, W. Giersch, B. Winter, H. Pamingle and G. Ohloff, Helv. Chim. Acta, 1985, 68, 1961; H. Hagiwara and H. Uda, J. Chem. Soc., Chem. Commun., 1988, 815.
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17. 2using Shelx97 (non-hydrogen atoms anisotropic and hydrogen atoms isotropic in calculated positions). Final R = 9.46, weighted R = 2.75. Crystal data have been deposited at the Cambridge Crystallographic Data Centre.
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19. For related synthetic approaches see R. Esmond, B. Fraser Reid and B. B. Jarvis, J. Org. Chem., 1982, 47, 3358; A. Kanazawa, P. Declair, M. Pourashraf and A. E. Greene, J. Chem. Soc., Perkin Trans 1, 1997, 1911.
20. All novel compounds isolated gave spectroscopic data in accord with their assigned structures.
21. The (R)-and (S)-enantiomers of 3-bromo-2-methyl propan-1-ol were purchased from Aldrich Chemical Co.
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26. 4, and concentrated under reduced pressure. The crude product was purified by flash column chromatography eluting with 15% ether in 30-40 petrol to furnish exclusively E-isomer.
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28. 4, and concentrated under reduced pressure. Purification by gradient flash column chromatography, eluting initially with 30-40 petrol, increasing to 5% ether : 95% 30-40 petrol afforded the coupled product as a colourless oil.
29. We are grateful to Professor R. Capon of the University of Melbourne for providing us with copies of the spectra for this compound.
30. 2using Shelx97 (non-hydrogen atoms anisotropic and hydrogen atoms isotropic in calculated positions). Final R = 5.95, weighted R = 2.63. Crystal data have been deposited at the Cambridge Crystallographic Data Centre.