Total synthesis of (-)-kaitocephalin

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4165-4167

  Kawasaki, Masanori ^a   Shinada, Tetsuro ^a   Hamada, Makoto ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KAITOCEPHALIN; LACTAM; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

LACTAMS; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 25444457793     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0515154     Document Type: Article

References (27)

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15. Addition of an enolate derived from a glycine ester to 3 resulted in a deformylation to give methyl pyroglutamate.
16. The structure to have 2S,3S configuration was determined by converting it to a bicyclic derivative (Supporting Information).
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20. 1H NMR spectrum and HPLC profile were not identical to that of natural 1 (Supporting Information).
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23. The stereoselectivity would be explained by a proposed model 21 in which the electron-rich ether oxygen is participating to form a chelate complex with copper (Scheme 3). Formation of a copper complex in the allylation of 16a with an organocopper reagent was discussed. Skrinjar, M.; Wistrand, L.-G. Tetrahedron 1991, 47, 573-582.
24. The structures of the R-isomers 22ab-24ab are depicted in Scheme 3.
25. 3P in view of its faster reaction rate, better yields, and easy removal of the resulting phosphine oxide.
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27. A C7 isomer of 26 was used for the removal of the protecting groups as a model. The C4 methyl ester was found to be resistant to alkaline hydrolysis (1 N NaOH or 1 N LiOH). Upon exposure to 30% HBr, a spirolactam was formed between the C2 amino and C4 ester groups.