Aldol condensation reactions of chiral (dienone) tricarbonyliron complexes. 2. Enantioselective synthesis of the dienic polyols streptenols C and D (metabolites from streptomyces fimbriatus).

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4469-4472

  Franck Neumann, Michel ^a   Bissinger, Paul ^a   Geoffroy, Philippe ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

STREPTOMYCES FIMBRIATUS;

EID: 0030976798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00904-0     Document Type: Article

References (20)

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2. a/ Kuhn, D.E.; Lillya, C.P. J. Am. Chem. Soc., 1972 94, 1682 and ref. therein.
3. b/ Franck-Neumann, M.; Chemla, P.; Martina, D. Synlett, 1990 641.
4. a/ Arnone, A.; Candillo, R.; Nasini, G.; Vajna de Pava, O.; Quaroni, S. Phytochemistry 1988, 27, 3611.
5. b/ Niederer, D.; Séquin, U.; Drautz, H.; Zähner, H. Helv. Chim. Acta 1990, 73, 2129.
6. c/ Grabley, S.; Hammann, P.; Kluge, H.; Wink, J. J. Antibiot. 1991, 44, 797.
7. d/ Synthesis of Streptenol D : Hayashi, M.; Kaneda, H.; Oguni, N. Tetrahedron Asymmetry 1995, 6, 2511.
8. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
9. 2O, the selectivity was anew reversed in favor of the (S,R) diastereomer (3 : 1) !
10. 4, the β-benzyloxypropanals gave mainly the desired (S,S) ketols. However the selectivity was far better with an ortho-methoxybenzyl group (1 : 10), than with a paramethoxybenzyl group (1 : 5). The unsubstituted benzyl ether also gave good selectivity (1 : 10), but we were unable to achieve deprotection by catalytic hydrogenation, and switched therefore to the methoxylated series and oxidative deprotection.
11. Franck-Neumann, M.; Briswalter, C.; Chemla, P.; Martina, D. Synlett 1990, 637.
12. The detailled preparation, to be described in a full paper dealing with the synthesis of various optically active α-heterosubstituted dienone complexes, follows the procedures of Hase, T.A.; Salonen, K. Synth. Comm. 1980, 10, 221 and Melilo, P.G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783.
13. The detailled preparation, to be described in a full paper dealing with the synthesis of various optically active α-heterosubstituted dienone complexes, follows the procedures of Hase, T.A.; Salonen, K. Synth. Comm. 1980, 10, 221 and Melilo, P.G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783.
14. 15 and oxidation (PCC).
15. 3, 200 MHz, ppm/TMS, Hz) : (+)-5 : δ = 1.22 (dd, 1H, J = 8.2 and 0.7), 1.47 (d, 3H, J = 5.8), 1.54 (m, 1H), 1.72-1.82 (m, 2H), 2.50 (dd, 1H, J = 16.3 and 5.2), 2.60 (dd, 1H, J = 16.3 and 7.3), 3.65-3.78 (m, 2H), 3.84 (s, 3H), 3.86 (d, 1H, J = 2.9), 4.23 (m, 1H), 4.55 (s, 2H), 5.24 (dd, 1H, J = 7.9 and 5.1), 5.79 (ddd, 1H, J = 8.3, 5.1 and 0.8), 6.87-7.29 (4H, arom) ; (+)-9 : δ = 1.17 (d, 1H, J = 8.3), 1.48 (d, 3H, J = 5.8), 1.57 (m, 1H), 1.63-1.80 (m, 2H), 2.54 (d, 2H, J = 6.1), 2.70 (s, 1H), 3.75 (d, 1H, J = 2.3), 3.81-3.84 (m, 2H), 4.26 (m, 1H), 5.26 (dd, 1H, J = 8.4 and 5.1), 5.79 (dd, 1H, J = 8.8 and 5.6) ; (+)-10 : δ = 1.08 (t, 1H, J = 7.7), 1.17 (m, 1H), 1.42 (d, 3H, J = 6.2), 1.70-1.90 (m, 4H), 2.28 (s, 2H), 3.33 (s, 1H), 3.70-3.90 (m, 3H), 4.25 (m, 1H), 5.07 (dd, 1H, J = 8.4 and 5.4), 5.14 (dd, 1H, J = 8.3 and 5.3).
16. Rychnovsky, S.D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
17. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 889.
18. The same reaction after decomplexation of (+)-5 or (+)-6 gave respectively an acetal which was much more difficult to deprotect than the complex (+)-8, and a mixture of monoprotected and acetalized Streptenol C, by oxidation of the allylic alcohol function.
19. 13.
20. Takano, S.; Ariyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593.