Asymmetric synthesis of the C(10)-C(16) segment of the bryostatins

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7695-7698

  Lampe, Thomas F J ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030597172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01759-5     Document Type: Article

References (16)

1. 1. Pettit, G. R.; Leet, J. E.; Herald, C. L.; Kamano, Y.; Boettner, F. E.; Baczynskyj, L.; Nieman, R. A. J. Org. Chem., 1987, 52, 2854; Pettit, G. R. The Chemist, 1989, 11.
2. 1. Pettit, G. R.; Leet, J. E.; Herald, C. L.; Kamano, Y.; Boettner, F. E.; Baczynskyj, L.; Nieman, R. A. J. Org. Chem., 1987, 52, 2854; Pettit, G. R. The Chemist, 1989, 11.
3. 2. a) Norcross, R. D.; Paterson, I. Chem. Rev., 1995, 95, 2041 and references cited therein;
4. b) Hoffmann, R. W.; Stiasny, H. C. Tetrahedron Lett., 1995, 36, 4595;
5. c) Kalesse, M.; Eh, M. Tetrahedron Lett., 1996, 37, 1767.
6. 3. Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc., 1990, 112, 7407.
7. 4. Lampe, T. F. J.; Hoffmann, H. M. R. Chem. Commun., 1996, 1931.
8. 5. For an innovative approach to 2,4,6-trifunctionalized C-glycosides see: Lampe, T. F. J.; Hoffmann, H. M. R, Bornscheuer, U. T. Tetrahedron: Asymmetry, 1996, 7, in press.
9. 6. An elegant solution for control of remote enoate geometry by use of a tethered HWE reagent giving a 14-membered, monounsaturated bislactone has been reported by: Evans, D. A.; Carreira, E. M. Tetrahedron Lett., 1990, 31, 4703.
10. 7. A more detailed study towards stereoselective olefination of cis-2,6-disubstituted tetrahydropyran-4-ones will be published elsewhere: Lampe, T. F. J.; Hoffmann, H. M. R. Chem. Comm., submitted.
11. 1H NMR and H-H-COSY spectra of a TBDMS-derivative of (+)-6; additional support was obtained from NOE experiments at 200 MHz.
12. 9. Kohli, V.; Blöcker, H.; Köster, H. Tetrahedron Lett., 1980, 21, 2683.
13. 2, 88 %.
14. 11. Various cyanohydrins with different protecting groups (EE, TBDMS, TES, TMS) have been investigated. The TES protected cyanohydrins performed extraordinary well with respect to: ease of formation, stability and reactivity of the corresponding anions and ease of unmasking in the presence of additional protecting groups.
15. 12. Shen, Q.; Sloss, D. G.; Berkowitz, D. B. Synth. Commun., 1994, 1519.
16. 7, 1.7), 285 (64), 199 (56), 135 (100).