A convenient preparation of elements of the stereotriade

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2773-2776

  Domon, L ^a   Vogeleisen, F ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL;

ACETYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029965487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00417-0     Document Type: Article

References (17)

1. a) Paterson, I.; Mansuri, M. Tetrahedron 1985, 41, 3569-3624;
2. b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry 1982, 13, 1-115;
3. c) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem. Inter. Ed. 1985, 24, 7-76.
4. a) Hoffmann, R. W. Angew. Chem. Inter. Ed. 1987, 26, 489-503;
5. b) Hoffmann, R. W.; Dahamann, G.; Andersen, M.W. Synthesis 1994, 629-638. For a recent synthesis of a anti,anti element of the stereotriade, see: Marshall, J. A.; Perkins, J. P.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556-5559. For an early exemple of utilisation of a syn,syn element in the synthesis of a polypropionate compound, see ref. 3c.
6. b) Hoffmann, R. W.; Dahamann, G.; Andersen, M.W. Synthesis 1994, 629-638. For a recent synthesis of a anti,anti element of the stereotriade, see: Marshall, J. A.; Perkins, J. P.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556-5559. For an early exemple of utilisation of a syn,syn element in the synthesis of a polypropionate compound, see ref. 3c.
7. a) Reformatsky, S. Chem. Ber. 1895, 3662-3665;
8. b) Gerzon, K.; Flynn, E. H.; Sigal, M. V.; Wiley, P. F.; Monaham, R.; Quarck, U. C. J. Am. Chem. Soc. 1956, 78, 6396-6408;
9. c) Mohr, P.; Tamm. C.; Gawronska, K.; Gawronski, J. K. Helv. Chim. Acta 1983, 66, 2501-2511;
10. d) Gawronski, J. K. Tetrahedron Lett. 1984, 25, 2605-2608;
11. e) Homes, D. S.; Sherringham, J. A.; Dyer, V. C.; Russell, S. T.; Robinson, J. A. Helv. Chim. Acta 1990, 73, 239-259;
12. f) Adjé, N.; Breuilles, P; Uguen, D. Tetrahedron Lett. 1992, 33, 2151-2154.
13. 3:MeOH): i) syn,syn-2: 0.25; ii) d/l-2: 0.35; iii) anti,anti-2: 0.4. The triol anti,anti-2 can also be obtained by 9-BBN hydroboration of 2,4-dimethyl-1,4-pentadiene-3-ol (Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A J. Org. Chem. 1992, 57, 1637-1639).
14. Breuilles, P.; Schmittberger, T.; Uguen, D. Tetrahedron Lett. 1993, 34, 4205-4208.
15. 13C NMR: 13.4, 14.5, 19.3, 29.6, 36.7, 67.6, 81.6. All the [α]D values reported herein have been recorded at 21°C. Candida cylindracea lipase-catalysed acetylation of the 3-O-TBDMS derivative of anti,anti-2 has been shown to occur exclusively on the pro-S branch (Chenevert, R.; Couchesne, L. Tetrahedron Asym. 1995, 6, 2093-2096).
16. 3 (≥0.2 eq.) to the NMR tube. Performing the same shift experiment with the optically active sulfides 5 described herein revealed the presence of only trace amount of the corresponding enantiomer (less than 3% by integration). Hence, the e.e. are better than 94%.
17. 3): 11.2, 19.8, 20.2, 29.1, 30.6, 31.7, 41.3, 43.9, 125.6, 128.9, 129, 137.8; 9-DNPH: m.p. 109-112°C ( lit.: m.p. 112-113°C (White, J. D.; Johnson, A. T. J. Org. Chem. 1994, 59, 3347-335)).