Studies directed toward the total synthesis of kabiramide C: Asymmetric synthesis of the C1-C19 fragment

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6147-6150

  Liu, Ping ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; KABIRAMIDE C; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; OXYGENATION; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032552197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01300-8     Document Type: Article

References (14)

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4. (b) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
5. (c) Celatka, C. A.; Liu, P.; Panek, J. S. Tetrahedron Lett. 1997, 38, 5449-5452.
6. 4. Mancuso, A. J.; Huang, S.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
7. 1H-NMR spectrum of the derived acetonide: (equation presented)
8. 6. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans, 1 1975, 1574-1585.
9. 7. VanRheenen, V.; Kelley, R. C.; Cha, D. J. Org. Chem. 1978, 43, 2480-2482.
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11. 9. The removal of the xanthate functionality in 11 was complicated due to the involvement of the proximal olefin bond, whereas the xanthate-removing operation of 12 proceeded smoothly.
12. 3).
13. 11. For recent applications of lithio-dithiane coupling in natural product synthesis, see Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961.
14. 1 the following transformation was observed: (equation presented)