메뉴 건너뛰기




Volumn 7, Issue 11, 2005, Pages 2265-2267

Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; TUBELACTOMICIN A; UNCLASSIFIED DRUG;

EID: 20444431520     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050763x     Document Type: Article
Times cited : (47)

References (23)
  • 8
    • 20444439700 scopus 로고    scopus 로고
    • note
    • Although a higher yield (92%) was realized when this reaction was carried out in neat DABCO, the reaction was completed after 30 days at room temperature. The coexistence of MeOH remarkably reduced the reaction time. We confirmed that 3-hydroxyquinuclidine (neat) also accelerates the reaction without a loss of the yield of 9.
  • 9
    • 0000516236 scopus 로고    scopus 로고
    • and references therein
    • For the acceleration of the Baylis-Hillman reaction in the presence of MeOH, see: Aggarwal, V. K.; Mereu, G. T.; Tarver, R.; McCague, R. J. Org. Chem. 1998, 63, 7183-7189 and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 7183-7189
    • Aggarwal, V.K.1    Mereu, G.T.2    Tarver, R.3    McCague, R.4
  • 11
    • 33845552447 scopus 로고
    • In place of DMPU, HMPA was also effective, although the yield of 11 was somewhat reduced. The phosphate-buffered solution was crucial to sustain the silyl protecting group. For the effect of the polar aprotic solvents, see: Hutchins, R. O.; Taffer, I. M. J. Org. Chem. 1983, 48, 1360-1362.
    • (1983) J. Org. Chem. , vol.48 , pp. 1360-1362
    • Hutchins, R.O.1    Taffer, I.M.2
  • 12
    • 20444433712 scopus 로고    scopus 로고
    • note
    • In the NOE experiment of 13, a remarkable (22%) signal enhancement of the CHO proton was observed when the β-vinyl proton was irradiated. Thus, the geometrical structures of 11-13 were ascertained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.