Spongistatin synthetic studies. 2. Assembly of the C(18-28) spiroketal

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8671-8674

  Smith III, Amos B ^a   Zhuang, Linghang ^a   Brook, Christopher S ^a   Lin, Qiyan ^a   Moser, William H ^a   Lee Trout, Robert E ^a   Boldi, Armen M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MACROLIDE; SPONGISTATIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030784540     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10500-7     Document Type: Article

References (21)

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2. b) Bai, R.; Taylor, G. F.; Cichacz, Z. A.; Herald, C. L.; Kepler, J. A.; Pettit, G. R.; Hamel, E. Biochemistry 1995, 34, 9714-9721.
3. Part 1: preceding Letter in this issue.
4. The 1987 version of the MM2 force field was employed in conjunction with the Macromodel program (version 3.1): a) Bowen, J. P.; Pathiaseril, A.; Profeta, S., Jr.; Allinger, N. L. J. Org. Chem. 1987, 52, 5162-5166. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134.
5. The 1987 version of the MM2 force field was employed in conjunction with the Macromodel program (version 3.1): a) Bowen, J. P.; Pathiaseril, A.; Profeta, S., Jr.; Allinger, N. L. J. Org. Chem. 1987, 52, 5162-5166. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134.
6. b) Still, W. C.; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lipton, M.; Liskamp, R.; Chang, G.; Hendrickson, T.; DeGunst, F.; Hasel, W. Department of Chemistry, Columbia University, New York, NY 10027.
7. For alternative approaches to the CD-ring spiroketal moiety, see: a) Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1997, 62, 2678-2679.
8. b) Paquette, L. A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122.
9. Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925-6926.
10. 13C NMR spectra, as well as appropriate parent ion identification by high resolution mass spectrometry.
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18. For an earlier example of stereocontrol at a spiroketal center via complexation with a metal ion, see: Williams, D. R.; Sit, S.-Y. J. Am. Chem. Soc. 1984, 106, 2949-2954.
19. 24a in spiroketal (-)-20.
20. Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795-2798.
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