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Volumn 7, Issue 12, 2005, Pages 2301-2304

Reductive coupling of terpenic allylic halides catalyzed by Cp 2TiCl: A short and efficient asymmetric synthesis of onocerane triterpenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; CHLORINE DERIVATIVE; HALIDE; SQUALENE DERIVATIVE; TERPENE DERIVATIVE; TERPENOID DERIVATIVE; TITANIUM DERIVATIVE; TRITERPENE DERIVATIVE;

EID: 20544435021     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050335r     Document Type: Article
Times cited : (57)

References (55)
  • 26
    • 0000945150 scopus 로고
    • (d) Baker, R. Chem. Rev. 1973, 73, 487-530.
    • (1973) Chem. Rev. , vol.73 , pp. 487-530
    • Baker, R.1
  • 44
    • 20544466595 scopus 로고    scopus 로고
    • note
    • This process represented the first direct synthesis of squalene by the coupling of two (E,E)-farnesyl units.
  • 45
    • 20544438764 scopus 로고    scopus 로고
    • see ref 1b
    • Procedure used in the opening of oxiranes; see ref 1b.
  • 47
    • 0035921040 scopus 로고    scopus 로고
    • Zhang, W. Tetrahedron 2001, 57, 7237-7262.
    • (2001) Tetrahedron , vol.57 , pp. 7237-7262
    • Zhang, W.1
  • 48
    • 20544443133 scopus 로고    scopus 로고
    • note
    • Reaction of 4c with Ti(III) in the presence of water led to the formation of a 16% yield of methyl (2E,6E)-2,6-dimethyl-2,6-octadienoate. With 4d, a 12% yield of methyl (2E,6Z)-2,6-dimethyl-2,6-octadienoate was obtained in the presence of 2,4,6-collidine hydrochloride. In both cases, the corresponding homocoupling products were also formed (Table 1, entries 9 and 10).
  • 49
    • 0037174453 scopus 로고    scopus 로고
    • Corey and co-workers have recently described a total synthesis of (+)-α-onocerin, see: Mi, Y.; Schreiber, J. V.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 11290-11291. Previous syntheses of onocerane derivatives, most relying on numerous steps, can be found in references cited in the above-mentioned paper.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11290-11291
    • Mi, Y.1    Schreiber, J.V.2    Corey, E.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.