Regio- and stereoselective functionalization of deltacyclenes: A route to the synthesis of optically active (+)-deltacyclan-8-one

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1129-1132

  Tenaglia, Alphonse ^a   Pardigon, Olivier ^a,b   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000668915     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951496j     Document Type: Article

References (33)

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31. This results perhaps that water is extensively hydrogen bonded and acts as a "large" nucleophile, as suggested by a reviewer.
32. R1+ = 79.9 min; the major enantiomer of 6b depicted in Scheme 2, which was eluted in second position, displays a positive rotatory power.
33. (+)-Deltacyclan-8-one (6b) was previously obtained by partial resolution from its morpholiminium perchlorate salt, see ref 3b, or kinetic resolution using reduction with microorganisms: Nakazaki, M.; Chikamatzu, H.; Fujii, T.; Nakatsuji, T. J. Org. Chem. 1981, 46, 585.