메뉴 건너뛰기




Volumn 54, Issue 25, 2015, Pages 7367-7370

Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight-Membered Cyclic Nitrone to Construct the 2-Azabicyclo[3.3.1]nonane Framework

Author keywords

alkaloids; cycloaddition; heterocycles; metathesis; natural products

Indexed keywords

ALKALOIDS; CARBON; CONDENSATION REACTIONS; CYCLOADDITION; KETONES;

EID: 84934973407     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501633     Document Type: Article
Times cited : (23)

References (48)
  • 2
    • 84890902117 scopus 로고    scopus 로고
    • (Ed.: H.-J. Knölker), Elsevier, Amsterdam, Chap.
    • B. Delpech, in The Alkaloids, Vol. 73 (Ed.:, H.-J. Knölker,), Elsevier, Amsterdam, 2014, Chap. 4, pp. 223-329.
    • (2014) The Alkaloids, Vol. 73 , pp. 223-329
    • Delpech, B.1
  • 29
    • 70350006015 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 2978-2981
    • (2006) Angew. Chem. , vol.118 , pp. 2978-2981
  • 31
    • 79953024916 scopus 로고    scopus 로고
    • For a review on the synthesis of 2-azabicyclo[3.3.1]nonanes, see.
    • For a review on the synthesis of 2-azabicyclo[3.3.1]nonanes, see:, J. Bonjoch, F. Diaba, B. Bradshaw, Synthesis 2011, 993-1018.
    • (2011) Synthesis , pp. 993-1018
    • Bonjoch, J.1    Diaba, F.2    Bradshaw, B.3
  • 32
    • 0030940424 scopus 로고    scopus 로고
    • Intermolecular cycloaddition of an eight-membered cyclic nitrone has been reported.
    • Intermolecular cycloaddition of an eight-membered cyclic nitrone has been reported:, S. S. Al-Jaroudi, H. P. Perzanowski, M. I. M. Wazeer, S. A. Ali, Tetrahedron 1997, 53, 5581-5592.
    • (1997) Tetrahedron , vol.53 , pp. 5581-5592
    • Al-Jaroudi, S.S.1    Perzanowski, H.P.2    Wazeer, M.I.M.3    Ali, S.A.4
  • 39
    • 0000122973 scopus 로고
    • Angew. Chem. 1971, 83, 355-357.
    • (1971) Angew. Chem. , vol.83 , pp. 355-357
  • 40
    • 85028228842 scopus 로고    scopus 로고
    • The isoxazolidine ring formed in the key cycloaddition reaction was strategically left to increase the steric bias for the ensuing formation of the quaternary stereogenic center.
    • The isoxazolidine ring formed in the key cycloaddition reaction was strategically left to increase the steric bias for the ensuing formation of the quaternary stereogenic center.
  • 41
    • 85028220657 scopus 로고    scopus 로고
    • The resulting aldehyde tended to epimerize during purification
    • The resulting aldehyde tended to epimerize during purification.
  • 42
    • 85028232936 scopus 로고    scopus 로고
    • The formation of hemiacetal 20 effectively prevented the Cannizzaro reaction of the aldol product
    • The formation of hemiacetal 20 effectively prevented the Cannizzaro reaction of the aldol product.
  • 47
    • 85028225488 scopus 로고    scopus 로고
    • The hydroxy group was likely to work as an internal base to assist the regioselective elimination
    • The hydroxy group was likely to work as an internal base to assist the regioselective elimination.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.