Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4203-4206

  Sakamoto, Yasuharu ^a   Shiraishi, Akiko ^a   Seonhee, Jeong ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Azides; Oxazolidinones; Sharpless asymmetric dihydroxylation; Stereocontrol

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; 4 EPICYTOXAZONE; AZIDE; CARBONIC ACID DERIVATIVE; CYTOXAZONE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYTOKINE RESPONSIVE ELEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; ISOMER; REDUCTION; STEREOISOMERISM;

EID: 0033612178     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00712-1     Document Type: Article

References (23)

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3. Sakamoto Y, Shiraishi A, Nakata T, Kakeya H, Osada H. 74th Spring Meeting of the Japan Chemical Society, 1998: Abstract 3E737.
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7. For a review, see: (b) Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483-2547.
8. Ethyl p-methoxycinnamate (6) is commercially available from Tokyo Kasei Co., Ltd.
9. The optical purity of the resulting diol ester was determined chromatographically with a Chiralcel OJ HPLC column (Daicel Chemical Technologies).
10. A similar result was reported, see: Lohray BB, Kalantar TH, Kim BM, Park CY, Shibata T, Wai JSM, Sharpless KB. Tetrahedron Lett. 1989; 30: 2041-2044.
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15. It is not obvious whether this oxazolidinone formation proceeds stepwise via hydrolysis of the resulting im-inophosphorane to an amine followed by nucleophilic cyclization or, alternatively, via the Staudinger-aza-Wittig cyclization [11] followed by hydrolysis of the resulting oxazoline.
16. For a review, see: Molina P, Vilaplana MJ. Synthesis 1994, 1197-1218.
17. 4: C, 59.19; H, 5.87; N, 6.27. Found: C, 59.21; H, 5.87; N, 6.35.
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22. 3, the migration of the ethoxycarbonyl group took place to form a non-cyclic carbamate at the C-4 position (53%). The resulting carbamate was also converted to the 2-oxazolidinone 16 with NaH in THF at room temperature (68%).
23. 4: C, 59.19; H, 5.87; N, 6.27. Found: C, 58.93; H, 5.88; N, 6.20.