메뉴 건너뛰기




Volumn 8, Issue 8, 2006, Pages 1609-1612

De novo asymmetric synthesis of D- and L-swainsonine

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SWAINSONINE;

EID: 33646438221     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0602811     Document Type: Article
Times cited : (108)

References (45)
  • 7
    • 0034721683 scopus 로고    scopus 로고
    • For a review of swainsonine syntheses, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579-8629.
    • (2000) Tetrahedron , vol.56 , pp. 8579-8629
    • Nemr, A.E.1
  • 24
    • 0026317511 scopus 로고
    • For the bioactivities of swainsonine, see: (a) Elbein, A. D. FASEB J. 1991, 5, 3055-3063.
    • (1991) FASEB J. , vol.5 , pp. 3055-3063
    • Elbein, A.D.1
  • 33
    • 0017494276 scopus 로고
    • An Achmatowicz reaction is the oxidative rearrangement of furyl alcohols to 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones; see: (a) Achmatowicz, O.; Bielski, R. Carbohydr. Res. 1977, 55, 165-176.
    • (1977) Carbohydr. Res. , vol.55 , pp. 165-176
    • Achmatowicz, O.1    Bielski, R.2
  • 34
    • 24944541990 scopus 로고    scopus 로고
    • and references therein
    • For its recent use in carbohydrate synthesis, see: (b) Guo, H.; O'Doherty, G. A. Org. Lett. 2005, 7, 3921-3924 and references therein.
    • (2005) Org. Lett. , vol.7 , pp. 3921-3924
    • Guo, H.1    O'Doherty, G.A.2
  • 35
    • 33646447162 scopus 로고    scopus 로고
    • note
    • In the Fleet synthesis of swainsonine a similar reductive amination was employed; see ref 5.
  • 36
    • 33646454213 scopus 로고    scopus 로고
    • note
    • While we have prepared both D- and L-swainsonine, for simplicity herein we only show the L-enantiomer.
  • 37
    • 0347022328 scopus 로고    scopus 로고
    • 3N (1:1 instead of 2:1) was required for the Noyori reduction of compounds with primary TBS groups; see: Li, M.; Scott, J. G.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 1005-1009.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1005-1009
    • Li, M.1    Scott, J.G.2    O'Doherty, G.A.3
  • 42
    • 25844446180 scopus 로고    scopus 로고
    • Presumably, because of the rigid nature of the 7 and the equatorial nature of the allylic azide no [3,3] sigmatropic rearrangement was observed; see: Feldman, A. K.; Colasson, B.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 13444-13445.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 13444-13445
    • Feldman, A.K.1    Colasson, B.2    Sharpless, K.B.3    Fokin, V.V.4
  • 45
    • 33646439209 scopus 로고    scopus 로고
    • note
    • By simply switching the (S,S)-Noyori reagent for the reduction of 10 to (ent)-9 to the (R,R)-Noyori reagent (10 to 9), D-swainsonine was prepared from 9 in nearly identical overall yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.