Total Synthesis of Petrosin, Petrosin A, and Petrosin B

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5001-5012

  Scott, Robert W ^a   Epperson, James ^a   Heathcock, Clayton H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000877160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801768     Document Type: Article

References (26)

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4. For an excellent recent review of this structurally unique class of marine natural products, see: Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proc. Int. 1998, 1-51.
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6. Calculated molecular mechanics energies of these 24 structures are included in the Supporting Information.
7. Prior work did not actually distinguish between structures 3 and 7 for petrosin B.
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11. Hoye and co-workers have reported a thermodynamically controlled synthesis of the biosynthetically related compound xestospongin A: Hoye, T. R.; North, J. T.; Yao, L. J. J. Am. Chem. Soc. 1994, 116, 2617. Hoye, T. R.; Ye, Z.; Yao, L. J.; North, J. T. J. Am. Chem. Soc. 1996, 118, 12074.
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25. A control experiment where the bis-imine was formed and subsequently hydrolyzed showed that negligible equilibration occurs during this step.
26. 13C NMR spectra. However, the data as presented are still useful for structure determination.