Total synthesis of hemibrevetoxin B

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6365-6368

  Morimoto, Masamichi ^a   Matsukura, Hiroko ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HEMIBREVETOXIN B; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030603086     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01373-1     Document Type: Article

References (26)

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15. 9. We have recently found that the (chloromethylsulfonyl)oxy group served as an efficient leaving group for the inversion of secondary alcohols. (a) Hiranuma, S.; Shimizu, T.; Nakata, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 8247.
16. (b) Shimizu, T.; Hiranuma, S.; Nakata, T. submitted.
17. 5
18. 11. The yield of the double rearrangement-ring expansion for 3 was improved using bis-chloromethanesulfonate 4 instead of the corresponding bis-mesylate reported in ref 5.
19. 12. The effective rearrangement-ring expansion of cyclic ethers having the (chloromethylsulfonyl)oxy group is now under investigation. The results will be reported in due course.
20. 13. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
21. 14. Highly stereoselective endo-cyclization of hydroxy styrylepoxides will be reported in due course.
22. 15. For a review on TPAP oxidation, see: Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
23. 1H NMR spectra: δ 4.40 (t, J=9.5 Hz; C7-H), 4.73 (ddd, J=4.9, 9.5, 11.6 Hz; C8-H).
24. 6
25. 18. A 2:1 mixture of 4α-and 4β-methoxy isomers.
26. 3b resulted in decomposition.