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Volumn 8, Issue 11, 2006, Pages 2353-2356

A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues

Author keywords

[No Author keywords available]

Indexed keywords

ANISOMYCIN; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; PALLADIUM; PREUSSIN;

EID: 33745711813     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0606435     Document Type: Article
Times cited : (63)

References (38)
  • 7
    • 33745716315 scopus 로고    scopus 로고
    • note
    • Kitahara has described a nonstereoselective route that affords all eight stereoisomers of preussin in a two-step sequence. The isomers were separated by preparative chiral HPLC. See ref 5.
  • 18
    • 33745730286 scopus 로고    scopus 로고
    • Reference 9b
    • Two strategies allow installation of the aryl moiety within 1-3 steps of the final target. Davis generated the C-2 benzyl group as the final step via reaction of lithium diphenyl cuprate with a pyrrolidinylmethyl iodide (40% yield, single diastereomer; 10 steps total, 9% overall yield). Bach employed a Paternò-Büchi reaction of benzaldehyde with a dihydropyrrole (4:1 dr, 53% yield after separation of diastereomers) followed by a two-step deprotection sequence to generate the benzyl substituent (39% over 3 steps; 9 steps total, 11% overall yield). See: (a) Reference 9b.
  • 20
    • 0034675654 scopus 로고    scopus 로고
    • To date, no analogues of preussin have been prepared that are modified on the aromatic ring. Bach has reported the synthesis of two analogues that differ in the nature of the C5 alkyl chain, and four analogues that differ in the nature of the C-3 substituent have been described in the patent literature. See: (a) Bach, T.; Brummerhop, H.; Harms, K. Chem. Eur. J. 2000, 6, 3838.
    • (2000) Chem. Eur. J. , vol.6 , pp. 3838
    • Bach, T.1    Brummerhop, H.2    Harms, K.3
  • 21
    • 33745702257 scopus 로고    scopus 로고
    • Jpn. Kokai. Tokkyo Koho 2003277357, 2003
    • (b) Suzuki, K.; Miike, N.; Kawamoto, E. Jpn. Kokai. Tokkyo Koho 2003277357, 2003.
    • Suzuki, K.1    Miike, N.2    Kawamoto, E.3
  • 28
    • 33645897192 scopus 로고
    • For a discussion of allylic strain related to the partial double bond character between the nitrogen atom and the carbonyl carbon in α-substituted amides and carbamates see: (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
    • (1989) Chem. Rev. , vol.89 , pp. 1841
    • Hoffmann, R.W.1
  • 33
    • 33745730290 scopus 로고    scopus 로고
    • note
    • Dpe-phos = bis(2-diphenylphosphinophenyl) ether.
  • 36
    • 33745702258 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.
  • 38
    • 33745702255 scopus 로고    scopus 로고
    • note
    • Use of high-purity starting material (>97% by NMR and GC) was essential to obtain high yields in reactions of electron-rich aryl bromides. Use of starting material with trace (ca 5%) impurities led to catalyst deactivation and formation of complex mixtures of products with these substrate combinations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.