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Volumn 63, Issue 12, 2007, Pages 2712-2723

Diastereoselective total synthesis of (+)-morusimic acid B, an amino acid from Morus alba

Author keywords

(+) Morusimic acid B; N Cyclization; Pyrrolidine amino acid

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; 3 HYDROXYBUTYRIC ACID METHYL ESTER; ACETIC ACID; ACETOACETIC ACID; AMINO ACID DERIVATIVE; ESTER DERIVATIVE; HYDRAZIDE DERIVATIVE; MERCURY; MORUSIMIC ACID B; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33846926121     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.008     Document Type: Article
Times cited : (8)

References (57)
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    • note
    • 1H NMR signals.
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    • and references cited therein
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    • 2, see e.g.:
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    • Solvomercuration/Demercuration Reactions in Organic Synthesis, Chapter VII
    • Springer, Berlin and references cited therein
    • Larock R.C. Solvomercuration/Demercuration Reactions in Organic Synthesis, Chapter VII. Amidomercuration (1986), Springer, Berlin 505-521 and references cited therein
    • (1986) Amidomercuration , pp. 505-521
    • Larock, R.C.1
  • 22
    • 33846909174 scopus 로고    scopus 로고
    • For N→π-cyclization with iodine, see:
  • 26
    • 33846894896 scopus 로고    scopus 로고
    • For N→π-cyclization with benzeneselenyl chloride, see:
  • 29
    • 33846908440 scopus 로고    scopus 로고
    • For Bronsted-acids catalysed N→π-cyclization, see:
  • 33
    • 33846936426 scopus 로고    scopus 로고
    • note
    • These compounds were synthesized by the same reaction sequence as 6 starting with the α-alkylation of β-hydroxyester 3 with 1-bromo-hex-2-ene and 1-bromo-undec-2-ene, respectively. Hydrazinolysis followed by Curtius rearrangement and N→π-cyclization with mercury(II) acetate gave the bicyclic compounds in 67% and 69% yields over four steps, respectively.
  • 34
    • 33846901068 scopus 로고    scopus 로고
    • note
    • Alkylation experiments with bromide 9 also afforded β-oxoester 11 but only in poor yields (20%). Therefore bromide 9 was converted to the more reactive iodide 10.
  • 36
    • 33846895113 scopus 로고    scopus 로고
    • For further examples of alkylations of β-keto ester dianions, see:
  • 45
    • 33846895854 scopus 로고    scopus 로고
    • For enantioselective reduction of β-keto esters with BINAP-Ru(II) complexes, also see:
  • 54
    • 33846924232 scopus 로고    scopus 로고
    • note
    • ®.
  • 55
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    • note
    • 1H NMR signals.
  • 56
    • 33846931032 scopus 로고    scopus 로고
    • note
    • According to Ref. 1 pharmacological activity regarding α-glucosidase inhibition could not be observed so far.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.