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Volumn 47, Issue 45, 1991, Pages 9329-9350

Total synthesis of (+)-monomorine I via nitrone cycloaddition route

Author keywords

(+) monomorine I; 1,3 dipolar cycloaddition; chiral allylic ether; inside alkoxy effect; nitrone

Indexed keywords

ALKALOID;

EID: 0025991695     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)80881-4     Document Type: Article
Times cited : (53)

References (83)
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    • (1978) Tetrahedron Lett. , pp. 737
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    • The nitrone cycloaddition with monosubstituted electron-rich dipolarophiles, incapable of secondary orbital interactions, proceed through exo transition states and are described as dipole LUMO controlled, resulting in 5-substituted isoxazolidines, A. Padwa, Wiley-Interscience, New York, Chapter 9
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2
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    • For rationalizing the stereochemical feature of electrophilic addition to allylic double bonds, similar transition state model referred to as OR in-plane (R = H, alkyl) model, in which OR group is in the plane of the allylic double bond, has been proposed
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7396
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    • During this reaction, cleavage of the N-benzyl group was recognized, which probably resulted in such low yield of 15.
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    • When the deketalization was performed with the secondary amine 20 under acidic conditions (HClMeOH), unfavorable formation of the bicyclic N,O-ketal i was observed.
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    • For the conversion of 25 to 26, if the hydrogenolysis of 25 was conducted in an acidic medium at the initial stage in the synthetic sequence, there would be a fear of unfavorable formation of the bicyclic N,O-ketal i (see ref. 24), incapable of undergoing reductive cyclization to 23, through the initial deblocking of the N- and O-benzyloxycarbonyl groups of 25 generating ii followed by spontaneous intramolecular ketalization under the reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.