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Volumn 4, Issue 2, 2009, Pages 277-285

Total synthesis of (-)- and (+)-decarbamoyloxysaxitoxin and (+-)-saxitoxin

Author keywords

1,3 dipolar cycloaddition; Guanidine; Natural products; Oxidation; Total synthesis

Indexed keywords

1,3-DIPOLAR CYCLOADDITION; [CARBONYL; ENANTIOSELECTIVE TOTAL SYNTHESIS; GUANIDINE; IMINIUM; NATURAL PRODUCTS; NITRO GROUPS; TOTAL SYNTHESIS;

EID: 59349116521     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800382     Document Type: Article
Times cited : (54)

References (60)
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    • Under the Swern oxidation conditions, C12 O-methyl thiomethyl (MTM) ether 59 was obtained in 79% yield. Figure presented
    • Under the Swern oxidation conditions, C12 O-methyl thiomethyl (MTM) ether 59 was obtained in 79% yield. Figure presented
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    • See the Supporting Information
    • See the Supporting Information.
  • 38
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    • Nicolaou et al. reported that IBX can oxidize alcohols, ketones, and aldehydes lo lhe corresponding α,β-unsalurated systems through enol formation of a carbonyl group and subsequent single-electronlransfer (SET) based oxidation reaction. See: a) K. C Nicolaou, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597;
    • Nicolaou et al. reported that IBX can oxidize alcohols, ketones, and aldehydes lo lhe corresponding α,β-unsalurated systems through enol formation of a carbonyl group and subsequent single-electronlransfer (SET) based oxidation reaction. See: a) K. C Nicolaou, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597;
  • 41
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    • Oxidation of alcohol 24 was difficult even though it has a less bulky group, and
    • Oxidation of alcohol 24 was difficult even though it has a less bulky group, NHBoc, at C5 than bis(guanidine) compounds 14 and 19.
    • NHBoc, at C5 than bis(guanidine) compounds , pp. 14-19
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    • All these reactions were monitored by ESI mass spectrometry
    • All these reactions were monitored by ESI mass spectrometry.
  • 57
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    • Small amounts of C5 epimer 40 and oxime 41 were generated.
    • Small amounts of C5 epimer 40 and oxime 41 were generated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.