Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1167-1180

  Zanardi, Franca ^a   Battistini, Lucia ^a   Nespi, Marika ^a   Rassu, Gloria ^b   Spanu, Pietro ^b   Cornia, Mara ^c   Casiraghi, Giovanni ^a  

^a Dipto Farmaceutico dell'Univ   (Italy)

^b Ist per l'Applic delle Tecniche C   (Italy)

^c Dipto Chim Organ Industriale D   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROXYPROLINE; PROLINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029881497     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00123-1     Document Type: Article

References (19)

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3. b) Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Gasparri Fava, G.; Belicchi Ferrari, M.; Pelosi, G. Tetrahedron Asymmetry 1992, 3, 1035.
4. Casiraghi, G.; Spanu, P.; Rassu, G.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1994, 59, 2906.
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9. (a) Dho, J. C.; Fleet, G. W. J.; Peach, J. M.; Prout, K.; Smith, P. W. Tetrahedron Lett. 1986, 27, 3203.
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14. Quite unexpectedly, treatment of compound 12 with 40% aq HF led to complete deacetonidation of the molecule, leaving the TBS group unaltered.
15. 3 etherate treatment and the subsequent work-up manipulations. For a similar annulation involving an oxonium species, see: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem. 1995, 60, 2780.
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