Chemoenzymatic synthesis of (+)-aspicilin from chlorobenzene

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3583-3586

  Banwell, Martin G ^a   McRae, Kenneth J ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ASPICILIN; CATECHOL DERIVATIVE; CHLOROBENZENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; OXYGENASE; TOLUENE DIOXYGENASE;

ARTICLE; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATECHOLS; CHLOROBENZENES; ESCHERICHIA COLI; INDICATORS AND REAGENTS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; OXYGENASES; STEREOISOMERISM;

EID: 0034676584     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006457v     Document Type: Article

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21. All new compounds had spectroscopic data [IR, UV (where appropriate), NMR, mass spectrum] consistent with those of the assigned structure. Satisfactory combustion and/or high-resolution mass spectral analytical data were obtained for new compounds and/or suitable derivatives.
22. Unless stated otherwise, specific rotations were recorded in chloroform at 22°C.
23. 3) δ 9.70 (d, J = 2.3 Hz, 1H), 5.81 (m, 1H), 5.15-5.02 (complex m, 2H), 4.30 (m, 2H), 3.82 (dd, J = 5.9 and 11.3 Hz, 1H), 2.42 (m, 1H), 2.23 (m, 1H), 1.58 (s, 3H), 1.39 (s, 3H), 0.88 (s, 9H) and 0.06 (s, 6H).
24. 41 a related approach to (+)-aspicilin.
25. 2Zn (2.2 molar equiv of a 2 M solution in toluene) and b, -78°C, warm to -25°C over 4 h; (iii) trimethyl phosphonoacetate (3.0 molar equiv), DMAP (0.3 molar equiv), toluene, 111°C, 14 h.
26. 12 and 10 with those determined (S. Hatakeyama, personal communication to M. G. Banwell) for their enantiomerically pure counterparts suggests that the phosphonate ester obtained by the present route to be of ca. 88% ee.
27. For a useful point-of-entry to the current literature on RCM processes, see: Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
28. 13 We attribute the selectivity associated with this Wadsworth-Emmons reaction to the operation of Horeau's amplification of chirality principle (see Rautenstrauch, V. Bull. Soc. Chim. Fr. 1994, 131, 515). Thus, when a stoichiometric excess of compound 10 is employed in this bimolecular process, there is, throughout the course of the reaction, a kinetic selection for condensation of the enantiomerically pure aldehyde 3 with the more abundant enantiomeric form of the sodium salt of phosphonoacetate 10.
29. Purchased from Strem Chemicals, Inc.
30. 15
31. For a comprehensive listing of the physical and spectroscopic properties of (+)-aspicilin, see: Huneck, S.; Yoshimura, I. Identification of Lichen Substances; Springer-Verlag: Berlin, 1996; p 137.