Novel route to the synthesis of hydroxylated pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde. Total synthesis of (+)-preussin

Heterocycles

Volumn 46, Issue 1, 1997, Pages 335-348

  Kadota, Isao ^a   Saya, Shioko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000391968     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s19     Document Type: Article

References (30)

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13. For the preliminary report of this work, see: I. Kadota, M. Kawada, S. Saya, and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 2109.
14. In general, γ-aminoallylstannanes exhibit lower reactivity toward aldehydes than γ-alkoxy-allylstannanes.
15. α and olefinic protons, 9a was converted to 10 via acetylation and hydrogenation.
16. 8 because of the broading of the signals at rt.
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28. 2 gave 16 in 73% yield.
29. Recently we have developed an efficient method for the synthesis of γ-alkoxyallylstannanes from sterically bulky substrates via an acetal cleavage. However, unfortunately, several attempts failed to synthesis the corresponding N.O-acetal from 16 and γ-methoxyallylstannane. See: I. Kadota, T. Sakaihara, and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 3195. Equation Presented
30. 8 because of the broading of the signals at rt