Studies in marine macrolide synthesis: Stereocontrolled synthesis of the AB-spiroacetal subunit of spongistatin 1 (altohyrtin A)

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8581-8584

  Paterson, Ian ^b   Oballa, Renata M ^a   Norcross, Roger D ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16144363676     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01961-2     Document Type: Article

References (30)

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2. (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
3. 2. (a) Pettit, G. R.; Herald, C. L.; Cichacz, Z. A.; Gao, F.; Schmidt, J. M.; Boyd, M. R.; Christie, N. D.; Boettner, F. E. J. Chem. Soc., Chem. Commun. 1993, 1805.
4. (b) Pettit, G. R.; Cichacz, Z. A.; Herald, C. L.; Gao, F.; Boyd, M. R.; Schmidt, J. M.; Hamel, E.; Bai, R. J. Chem. Soc., Chem. Commun. 1994, 1605.
5. 3. Some of the altohyrtin macrolides reported in the folowing papers are assumed to be structurally identical to the spongistatins (i.e. altohyrtin A corresponds to spongistatin 1): (a) Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243.
6. (b) Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795.
7. (c) Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989.
8. 4. Cinachyrolide A is assumed to be structurally identical to spongistatin 4 (see ref 2a): Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977.
9. 5. Pettit, G. R. Pure Appl. Chem. 1994, 66, 2271 and references therein.
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21. 6) 21.2, 30.4, 34.2, 35.0, 35.4, 36.7, 43.6, 45.4, 62.2, 62.6, 66.5, 66.7, 67.0, 67.4, 72.1, 72.2, 97.3, 127.4, 127.5, 127.7, 128.3, 138.3, 138.6, 169.9.
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24. 15. The 1,3-induction obtained with such boron-mediated aldol reactions of methyl ketones is influenced by several factors, one of which is the nature of the β-hydroxyl protecting group in the aldehyde. See also: (a) Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537.
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27. 2-symmetric compound.
28. 17. Paterson, I.; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 0000 (following paper).
29. 18. Alternatively, when 3 was oxidised to the acyclic β-diketone, all attempts to effect efficient spiroacetalisation failed.
30. 19. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.