Studies in marine macrolide synthesis: Synthesis of a C16-C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spisoacetal moiety

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8911-8914

  Paterson, Ian ^a   Wallace, Debra J ^a   Gibson, Karl R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; SPONGISTATIN 1; UNCLASSIFIED DRUG;

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

EID: 0030733069     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10483-X     Document Type: Article

References (23)

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8. Paterson, I.; Oballa, R. M.; Norcross, R. D. Tetrahedron Lett. 1996, 37, 8581.
9. For other synthetic efforts, see: (a) Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1997, 62, 2678.
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11. Paquette, L. A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115.
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13. 3) 209.3, 159.1, 130.5, 129.2, 113.7, 98.4, 73.9, 72.9, 72.6, 66.6, 65.1, 64.3, 55.6, 55.3,48.6,43.2, 37.0, 36.9, 35.5, 35.1, 25.9, 18.1, 7.7, -4.91, -4.95.
14. (a) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C.; J. Org. Chem. 1986, 51, 432.
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16. We thank Dr Renata Oballa for preparing the alcohol (R)-13.
17. (a) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46,4663.
18. (b) For a review, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
19. For high levels of 1,5-anti stereoinduction in related cases, see: (a) Paterson, I.; Gibson. K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 8585.
20. (b) Evans, D. A.; Coleman, P. J.; Cote, B. J. Org. Chem. 1997, 62,788.
21. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
22. tBu, led to formation of the undesired spiroacetal 25.
23. -1) than 16.