Stereocontrolled synthesis of the CD subunit of the marine macrolide altohyrtin A

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3895-3898

  Zemribo, Ronald ^a   Mead, Keith T ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; MALIC ACID; SPONGISTATIN 1; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032482491     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00686-8     Document Type: Article

References (19)

1. 1. (a) Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246.
2. (b) Kobayashi, M.; Aoki, S.; Gato, K.; Kitagawa, I. Chem. Pharm. Bull. 1996,44, 2142-2149.
3. 2. For a total synthesis of altohyrtin C (spongistatin 2), see: Evans, D. A.; Trotter, B. W.; Cote, B.; Coleman, P. J.; Dias, L. C.; Tyler, A. N. Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
4. 3. Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302-1304.
5. 4. Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977-3981.
6. 5. For previous synthetic work on the CD ring, see: (a) Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2738-2741.
7. (b) Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1997, 62, 2678-2679.
8. (c) Paquette, L. A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122.
9. (d) Smith, III, A. B.; Zhuang, L.; Brook C. S.; Lin, Q.; Moser, W. H.; Trout, R. E. L.; Boldi, A. M. Tetrahedron Lett. 1997, 38, 8671-8674.
10. (e) Paterson, I.; Wallace, D. J.; Gibson, K. R. Tetrahedron Lett. 1997, 38, 8911-8914.
11. 6. See preceding paper in this issue.
12. 7. Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Can. J. Chem. 1984, 62, 2146-2147.
13. 8. Nicolaou, K. C.; Webber, S. E.; Ramphal, J.; Abe, Y. Angew. Chem. Int. Ed. Engl. 1987, 26, 1019-1021.
14. 9. Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1995, 60, 8122-8123.
15. 10. Piers, E.; Chong, M. J. J. Chem. Soc., Chem. Commun. 1983, 934-935.
16. 11. Compound 21 was the only product formed when vinyl stannane 6a was treated with MeLi at -78°C. Analogous rearrangements were observed with both TBS and TBDMS protective groups. (Equation Presented)
17. 12. (a) Zemribo, R.; Romo, D. Tetrahedron Lett. 1995, 36, 4159-4162.
18. (b) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226.
19. 6, 75 MHz) δ 35.00, 37.57, 38.50, 40.81, 43.69, 51.37, 63.72, 67.03, 67.58, 69.68, 71.39, 76.91, 93.40, 99.75, 127.56, 127.85, 128.53, 139.26, 171.47, 208.39