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Volumn 38, Issue 7, 1999, Pages 971-974

A concise synthesis of fumagillol

Author keywords

Angiogenesis; Antitumor agents; Fumagillin; Natural products; Total synthesis

Indexed keywords

FUMAGILLIN; FUMAGILLOL; FUMAGILLOL CHLOROACETYLCARBAMATE;

EID: 0033119793     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W     Document Type: Article
Times cited : (41)

References (43)
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    • Very recently, Clardy and co-workers reported an X-ray crystal structure of human MetAP-2 covalently bound by fumagillin, see S. Liu, J. Widom, C. W. Kemp, C. M. Crews, J. Clardy, Science 1998, 252, 1324-1327.
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    • 1-Diethylamino-1,3-butadiene can be prepared on a large scale in one step from diethylamine and crotonaldehyde, see S. Hünig, H. Kahanek, Chem. Ber. 1957, 90, 238-245.
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    • Vinyl bromide 8 was prepared by a slight modification of the excellent one-flask procedure of Corey et al., see E. J. Corey, J. Lee, B. E. Roberts, Tetrahedron Lett. 1997, 38, 8915-8918.
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    • For reviews of the conjugate addition chemistry of organocuprates, see a) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631;
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    • (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, New York
    • b) J. A. Kozlowski in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, New York, 1991, pp. 169-198.
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    • note
    • 2, followed by fluoride-induced cleavage of the crude enol silyl ethers.
  • 41
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    • note
    • This is a slight modification of a procedure employed in Corey and Snider's pioneering synthesis of fumagillin (reference [6]).
  • 42
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    • 2Me) in optically active form is available from (-)-quinic acid (D. F. McComsey, B. E. Maryanoff, J. Org. Chem. 1994, 59, 2652-2654) or by Sharpless asymmetric dihydroxylation followed by isopropylidene ketal formation
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.