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Volumn 48, Issue 37, 2007, Pages 6556-6560

Deacetalisation-bicyclisation routes to novel polycyclic heterocycles using stannous chloride dihydrate

Author keywords

Bicyclisation; Deacetalisation; Heterocycles; Stannous chloride

Indexed keywords

INTEGRASE INHIBITOR; INTEGRASTATIN A; INTEGRASTATIN B; NATURAL PRODUCT; STANNOUS CHLORIDE; UNCLASSIFIED DRUG;

EID: 34547738465     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.018     Document Type: Article
Times cited : (18)

References (20)
  • 7
    • 73049119014 scopus 로고
    • It should be noted that a similar cyclisation was first reported by Winterfeld et al.: but this employed hydrochloric acid and was far less efficient
    • It should be noted that a similar cyclisation was first reported by Winterfeld et al.:. Winterfeld K., Michael H. Arch. Pharm. Ber. Dtsch. Pharm. Ges. (1961) 65-76 but this employed hydrochloric acid and was far less efficient
    • (1961) Arch. Pharm. Ber. Dtsch. Pharm. Ges. , pp. 65-76
    • Winterfeld, K.1    Michael, H.2
  • 8
    • 31544443516 scopus 로고    scopus 로고
    • For a related procedure using tosic acid see:
    • For a related procedure using tosic acid see:. Ijzendoorn D.R., Botman P.N.M., and Blaauw R.H. Org. Lett. 8 (2006) 239-242
    • (2006) Org. Lett. , vol.8 , pp. 239-242
    • Ijzendoorn, D.R.1    Botman, P.N.M.2    Blaauw, R.H.3
  • 13
    • 34547763159 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR and HRMS or elemental analysis.
  • 14
    • 34547736900 scopus 로고    scopus 로고
    • note
    • ®) a 41% overall yield was obtained; when HATU was employed the amide coupling step was unsuccessful.
  • 15
    • 34547729634 scopus 로고    scopus 로고
    • 9 (50 mg, 0.34 mmol) and N-methylpiperidine (41 μL, 0.34 mmol) in DCM (4 mL) at -10 °C. After 2 min, an ice cold solution of l-cysteine methyl ester hydrochloride 10a (62 mg, 0.36 mmol) and N-methylpiperidine (44 μL, 0.36 mmol) in DCM (1 mL) was added dropwise and stirring continued at -10 °C for 1 h and then at rt for a further 1 h. The solution was then filtered through a short pad of silica gel, washing through with EtOAc (3 × 5 mL) and the volatiles removed from the filtrate in vacuo to give the crude amide 8a, which was used immediately without further purification.
  • 16
    • 34547732336 scopus 로고    scopus 로고
    • 3S requires 202.0532.
  • 19
    • 0001067309 scopus 로고
    • For similar systems see: and Ref. 6c
    • For similar systems see:. Griot R.G., and Frey A.J. Tetrahedron 19 (1963) 1661-1673 and Ref. 6c
    • (1963) Tetrahedron , vol.19 , pp. 1661-1673
    • Griot, R.G.1    Frey, A.J.2
  • 20
    • 34547753431 scopus 로고    scopus 로고
    • note
    • In addition to Lewis acid activation provided by Sn(II), it is likely that HCl generated during the reaction plays a vital role (attempts to carry out the reactions in the presence of potassium carbonate were unsuccessful).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.