Dihydroxylation of polyenes using Narasaka's modification of the upjohn procedure

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7322-7327

  Gypser, Andreas ^a   Michel, Dominique ^a   Nirschl, David S ^a   Barry Sharpless, K ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000412027     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980850l     Document Type: Article

References (24)

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6. (a) Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345.
7. (b) Unlike the piecemeal sequence required for the earlier perdihydroxylation (ref 12), the Narasaka method allows for perdihydroxylation of squalene in a single step: Gypser, A.; Sharpless, K. B. Unpublished results.
8. In our previous paper (see ref 6a) we incorrectly reported the number of possible stereoisomers from exhaustive suprafacial dihydroxylation of the trans,trans,cis and trans,cis,cis isomers of 1,5,9cyclododecalriene. Both the trans,trans,trans and the trans,cis,cis isomers can result in three and not four different diastereomeric products (see scheme below). matrix equation presented
9. Hugger, U.; Sharpless, K B. Tetrahedron Lett. 1995, 36, 6603.
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14. VanRheenen, V.; Cha, D. Y.; Hartley, W. M. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. VI, p 342.
15. Narasaka reported the use of 2 mol % osmium, so the extraordinary activity present in his system went largely unnoticed.
16. Diastereomer ratio determined by GC analysis of the corresponding hexaacetate derivatives.
17. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K; Thorpe, A. J. Chem. Rev. 1996, 96, 1195.
18. The structures were assigned by exploiting the anti stereochemistry of one of the tetrols. The monotosylate of each tetrol was prepared, and the compound which cyclized to the bicyclic ethers 20 and 21 revealed its anti stereochemistry. See Experimental Section for details. . Matrix equation presented
19. Park, C. Y. Ph.D. Thesis, Massachusetts Institute of Technology, 1991.
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24. Powell, K. A.; Hughes, H.; Katchian, J. F.; Jerauld, J. F.; Sable, H. Z. Tetrahedron 1972,28, 2019. The syn/anti stereochemistry issue for the tetrol was not resolved. According to our results, they prepared the syn isomer, (1R*,2S*,5R*,6S*)-cyclooctane-l,2,5,6-tetrol.