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Volumn 45, Issue 33, 2006, Pages 5510-5515

Toward the total synthesis of spirastrellolide A. Part 2: Conquest of the northern hemisphere

Author keywords

Cycloaddition; Macrolides; Natural products; Phosphatase inhibitors; Total synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; MACROLIDE; SPIRASTRELLOLIDE A;

EID: 33748636245     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601655     Document Type: Article
Times cited : (77)

References (50)
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    • D. A. Evans, M. M. Morrissey, R. L. Dorow, J. Am. Chem. Soc. 1985, 107, 4346-4348; good results were obtained only when the reaction was performed at 50°C; otherwise, a competing attack of MeOMgBr at the carbamate carbonyl group of the substrate is observed, which lowers the yield of 6.
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    • note
    • Details will be reported in a forthcoming full paper.
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    • Reviews on the use of 2-isoxazolines as aldol surrogates: a) D. P. Curran, Adv. Cycloaddit. 1988, 1, 129-189;
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    • note
    • The time for deprotonation must be <5 minutes; otherwise, significant decomposition of the cyanohydrin part was observed. Likewise, the use of KHMDS as the base and hexamethyl phosphoramide (HMPA) as a cosolvent were detrimental.
  • 46
    • 33748651132 scopus 로고    scopus 로고
    • note
    • The configuration of the cyanohydrin center C31 has not been determined.
  • 50
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    • note
    • NMR spectroscopic analysis suggests that the compound mainly exists as a pyranoid hemiacetal analogous to that found in 35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.