Asymmetric total synthesis of (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.)

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2739-2742

  Pinard, Emmanuel ^a,b   Gaudry, Michel ^a   Hénot, Frédéric ^a   Thellend, Annie ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PHYTOALEXIN;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; HYDROXYLATION; NONHUMAN; PEA;

EID: 0032580423     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00299-8     Document Type: Article

References (27)

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22. 16. As much 10% PoVC as diol 9 in weight was used.
23. 17. Dehydration of 11 occurs easily under very mild acidic conditions. After filtration of the catalyst, the filtrate has to be neutralized with pyridine.
24. 18. A similar "hydrogenative cyclisation" was observed by Kapil during the synthesis of the natural coumestan tuberostan: Prasad Krishna, A.V.; Kapil, R.S.; Popli, S.P. J. Chem. Soc. Perkin Trans. I 1986, 1561-1563. Surprisingly, this type of cyclisation did not take place when the phenol located on the left side of diol 9 was protected as a methyl ether instead of a benzyl ether.
25. 1=11.6 min was not detected. Synthetic (+)-pisatin was thus optically pure.
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27. 21. (-)-pisatin was prepared following the same synthetic scheme and by using dihydroquinidine p-chlorobenzoate as chiral ligand for ihe dihydroxylation step.