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Volumn 7, Issue 13, 2005, Pages 2747-2750

Stereoselective synthesis of 2,6-disubstituted 3-piperidinols: Application to the expedient synthesis of (+)-julifloridine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; JULIFLORIDINE; PIPERIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE;

EID: 27644547805     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051022z     Document Type: Article
Times cited : (72)

References (69)
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    • Camps, F.; Coll, J.; Messeauer, A.; Pujol, F. J. Org. Chem. 1982, 47, 5402-5404. 2-Propanol was used as a nucleophile since methanol is described to be incompatible with this epoxidation procedure. Furthermore, both nucleophiles were shown to cleanly react with 12 (with DMDO, see Table 2).
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    • note
    • Cis product is the kinetic product since treatment of 13a with TFA in EtOH for 76 h led to the 2,3-trans-ethanol adduct in 74% yield.
  • 56
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    • For a related cis stereoselective glycal epoxide opening using organozinc triflate or organozinc chloride, see: Xue, S.; Han, K.-Z.; Guo, Q.-X. Synlett 2003, 870-872.
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  • 65


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.