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Volumn 42, Issue 40, 2003, Pages 4961-4966

A Concise and Flexible Total Synthesis of (-)-Diazonamide A

Author keywords

Antimitotic agents; Natural products; Oxidation; Photochemistry; Total synthesis

Indexed keywords

POLYPEPTIDES; PROTEINS;

EID: 0242323632     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352577     Document Type: Article
Times cited : (218)

References (51)
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    • Ring closure in 5 could also occur via its phenol tautomer.
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    • Geometry optimization of 6 (R = Ac) was performed by using the Amber force field within Macromodel v7.0 (Schrödinger). The result was subjected to a Monte Carlo molecular dynamics simulation. Figure 1 depicts rigid superimposition of the ten lowest energy conformations calculated from this exercise.
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    • C11 stereochemistry, relative to C10, is governed by geometry. Only two cis-fused dihydrobenzofuro[2,3b] indole diastereomers are formed. C10-(R), C11-(S) diastereomer 15 has been characterized by X-ray diffraction (Scheme 2). CCDC-218220 (15) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.a-c.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
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    • 2O gradient) but partially degrade during flash chromatography on silica gel.
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    • 2. > 95% yield).
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    • We are grateful to Professor William Fenical (Scripps Oceanographic Institute) for a generous gift of natural (-)-diazonamide A.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.