메뉴 건너뛰기




Volumn 3, Issue 9, 2001, Pages 1383-1386

Total synthesis of (-)-ratjadone

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PYRONE DERIVATIVE; RATJADONE;

EID: 0035799895     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015753k     Document Type: Article
Times cited : (60)

References (59)
  • 1
    • 0000701347 scopus 로고    scopus 로고
    • Grabley, S., Thericke, R., Eds.; Springer: Berlin
    • For a review and some recent reports: (a) Reichenbach, H.; Höfle, G. Drug Discovery from Nature; Grabley, S., Thericke, R., Eds.; Springer: Berlin, 1999; pp 149-179.
    • (1999) Drug Discovery from Nature , pp. 149-179
    • Reichenbach, H.1    Höfle, G.2
  • 31
    • 0030839481 scopus 로고    scopus 로고
    • Related experiences in our rhizoxin total synthesis had forced us to adapt a plan for use of a sterically demanding tert-butyldimethylsilyl ether to avoid α-hydrogen abstraction. See: Williams, D. R.; Werner, K. M.; Feng, B. Tetrahedron Lett. 1997, 38, 6825.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6825
    • Williams, D.R.1    Werner, K.M.2    Feng, B.3
  • 34
    • 0000560517 scopus 로고
    • Reports of stereo- and regiocontrolled intramolecular openings of allylic oxiranes have provided an important advance in the synthesis of cyclic ethers. See: (a) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Huang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5330
    • Nicolaou, K.C.1    Prasad, C.V.C.2    Somers, P.K.3    Huang, C.-K.4
  • 36
    • 0344361923 scopus 로고
    • (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Huang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335. For Baldwin's rules: Baldwin, J. J. Chem. Soc., Chem. Commun. 1976, 734.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 734
    • Baldwin, J.1
  • 37
    • 0042120380 scopus 로고    scopus 로고
    • note
    • (a) These NOE studies were unsuccessful in the presence of the PMB ether.
  • 40
    • 0043122339 scopus 로고    scopus 로고
    • note
    • 4). providing a separable mixture of C16 isomers favoring the Cram chelation product 10.
  • 47
    • 0043122338 scopus 로고    scopus 로고
    • note
    • 7 methylene hydrogens as indicated below.
  • 57
    • 0043122337 scopus 로고    scopus 로고
    • note
    • Alternative protection schemes led to sulfone elimination yielding the (E)-unsaturated aldehyde, thus thwarting lactol formation. Unfortunately the TES ether did not withstand conditions leading to 25.
  • 59
    • 0041619560 scopus 로고    scopus 로고
    • note
    • Since our studies had previously led to isomers 9 and 10, which were not readily distinguished from reported data for the natural product, we are particularly grateful to Professor Gerhard Höfle (GBF, Braunschweig, Germany) for generously assisting these efforts by providing a pure sample of (+)-ratjadone for our direct comparisons.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.