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Volumn 49, Issue 49, 2010, Pages 9492-9495

Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B

Author keywords

carbasugars; electrocyclic ring closure; jadomycin; total synthesis

Indexed keywords

AGLYCONES; CARBASUGARS; ELECTROCYCLIC RINGS; GLYCOSIDIC BOND; JADOMYCIN; RING CLOSURES; RING SYSTEMS; TOTAL SYNTHESIS;

EID: 78650090998     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005329     Document Type: Article
Times cited : (70)

References (33)
  • 5
    • 78650079660 scopus 로고    scopus 로고
    • It has been suggested that the L -digitoxose sugar is attached to the aglycon by the enzyme JadS both before and after the oxazolone ring formation, see
    • It has been suggested that the L -digitoxose sugar is attached to the aglycon by the enzyme JadS both before and after the oxazolone ring formation, see
  • 17
    • 58149142847 scopus 로고    scopus 로고
    • For examples of diastereoselective aza-triene electrocyclic ring closures in synthesis, see.
    • For examples of diastereoselective aza-triene electrocyclic ring closures in synthesis, see:, G. Li, R. P. Hsung, B. W. Slafer, I. K. Sagamanova, Org. Lett. 2008, 10, 4991.
    • (2008) Org. Lett. , vol.10 , pp. 4991
    • Li, G.1    Hsung, R.P.2    Slafer, B.W.3    Sagamanova, I.K.4
  • 19
    • 78650122574 scopus 로고    scopus 로고
    • We found that most Brønsted/Lewis acid conditions for MOM/BOM groups removal lead to decomposition of starting material. We experienced similar problems with the hydrogenolysis of the BOM group. After some careful study we found a small window of opportunity with the short-term exposure (4-8 min) of both the MOM- and BOM-ether to concentrated HCl/acetonitrile (v/v 1:5).
    • We found that most Brønsted/Lewis acid conditions for MOM/BOM groups removal lead to decomposition of starting material. We experienced similar problems with the hydrogenolysis of the BOM group. After some careful study we found a small window of opportunity with the short-term exposure (4-8 min) of both the MOM- and BOM-ether to concentrated HCl/acetonitrile (v/v 1:5).
  • 27
    • 67650727208 scopus 로고    scopus 로고
    • Jakeman et al. reported similar color changes, see.
    • Jakeman et al. reported similar color changes, see:, D. L. Jakeman, S. N. Dupuis, C. L. Graham, Pure Appl. Chem. 2009, 81, 1041.
    • (2009) Pure Appl. Chem. , vol.81 , pp. 1041
    • Jakeman, D.L.1    Dupuis, S.N.2    Graham, C.L.3
  • 33
    • 78650105328 scopus 로고    scopus 로고
    • The route is 20 longest linear steps from quinic acid but only nine steps from known starting material 36.
    • The route is 20 longest linear steps from quinic acid but only nine steps from known starting material 36.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.