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Volumn 53, Issue 50, 2014, Pages 13826-13829

A cascade strategy enables a total synthesis of (-)-gephyrotoxin

Author keywords

Alkaloids; Asymmetric synthesis; Cascade reactions; Gephyrotoxin; Total synthesis

Indexed keywords

ALKALOIDS; CRYSTAL STRUCTURE; SINGLE CRYSTALS; X RAY DIFFRACTION;

EID: 84919388146     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409038     Document Type: Article
Times cited : (22)

References (51)
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    • 19F NMR spectroscopy (see the Supporting Information for full details). This result is consistent with our synthetic (-)-gephyrotoxin 14 sample being produced as a single enantiomer
    • 19F NMR spectroscopy (see the Supporting Information for full details). This result is consistent with our synthetic (-)-gephyrotoxin 14 sample being produced as a single enantiomer.
  • 45
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    • This is an average of three measurements
    • This is an average of three measurements.
  • 46
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    • We have derivatized 12 to intersect with Kishi's route. Our material has the opposite sign of optical rotation to that prepared by Kishi; see the Supporting Information for details
    • We have derivatized 12 to intersect with Kishi's route. Our material has the opposite sign of optical rotation to that prepared by Kishi; see the Supporting Information for details.
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    • An intermediate from the Kishi synthesis has been successfully resynthesized in both enantiomeric forms by several groups (see Ref. [11 a-f] for details). This confirms the relative and absolute configuration of this intermediate
    • An intermediate from the Kishi synthesis has been successfully resynthesized in both enantiomeric forms by several groups (see Ref. [11 a-f] for details). This confirms the relative and absolute configuration of this intermediate.
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    • Installation of the correct C1 side chain earlier in the synthesis was achieved, but attempts to perform a directed iminium reduction on this material led to exclusive generation of the non-natural 9, 10-trans stereochemistry, and so this approach was abandoned
    • Installation of the correct C1 side chain earlier in the synthesis was achieved, but attempts to perform a directed iminium reduction on this material led to exclusive generation of the non-natural 9, 10-trans stereochemistry, and so this approach was abandoned.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.