메뉴 건너뛰기




Volumn 120, Issue 11, 1998, Pages 2553-2562

Total synthesis of spinosyn A. 2. Degradation studies involving the pure factor and its complete reconstitution

Author keywords

[No Author keywords available]

Indexed keywords

INSECTICIDE;

EID: 0032565076     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974010k     Document Type: Article
Times cited : (57)

References (47)
  • 2
    • 2642617084 scopus 로고    scopus 로고
    • Spinosyn A is presently being marketed by DowElanco Inc.
    • Spinosyn A is presently being marketed by DowElanco Inc.
  • 3
    • 2642701818 scopus 로고    scopus 로고
    • 7) have been recently abandoned in favor of spinosyn A (Kirst, H. A.; communication dated June 7, 1994)
    • 7) have been recently abandoned in favor of spinosyn A (Kirst, H. A.; communication dated June 7, 1994).
  • 4
    • 2642613769 scopus 로고    scopus 로고
    • The LY232105 label was assigned following initial discovery of this secondary metabolite in the Eli Lilly laboratories
    • The LY232105 label was assigned following initial discovery of this secondary metabolite in the Eli Lilly laboratories.
  • 7
    • 2642676149 scopus 로고
    • Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4497
  • 8
    • 2642675357 scopus 로고    scopus 로고
    • The authors thank Dr. Graham F. Smith for these studies
    • The authors thank Dr. Graham F. Smith for these studies.
  • 20
    • 2642708475 scopus 로고    scopus 로고
    • (b) Rubottom, G. M.; Gruber, J. M.; Juve, H. D., Jr.; Charleson, D. A. Organic Syntheses; Wiley: New York, 1990; Coll. Vol. VII, p 282.
    • Organic Syntheses , vol.7 COLL , pp. 282
  • 21
    • 2642640548 scopus 로고    scopus 로고
    • Unpublished work from this laboratory
    • Purdie, M. Unpublished work from this laboratory.
    • Purdie, M.1
  • 22
    • 2642607131 scopus 로고    scopus 로고
    • Unpublished work from this laboratory
    • Collado, I. Unpublished work from this laboratory.
    • Collado, I.1
  • 23
    • 2642647183 scopus 로고    scopus 로고
    • NOE experiments designed to reveal the stereochemistry of this αβ-epoxy ketone proved not to be definitive
    • NOE experiments designed to reveal the stereochemistry of this αβ-epoxy ketone proved not to be definitive.
  • 24
    • 2642642229 scopus 로고    scopus 로고
    • note
    • In an effort to bypass lactol formation as in 20, the primary hydroxyl group in 19 was protected as the PMB derivative. This intermediate was not utilized further when it was recognized that oxidative cleavage of its 1,2-diol moiety with sodium periodate provided the aldehyde in only 22% yield for the two steps.
  • 25
    • 2642638880 scopus 로고    scopus 로고
    • Remarkably, when lithium hexamethyldisilazide was employed as the base, only the corresponding ring-closed silyl acetal was produced (92%) as a mixture of two isomers
    • Remarkably, when lithium hexamethyldisilazide was employed as the base, only the corresponding ring-closed silyl acetal was produced (92%) as a mixture of two isomers.
  • 26
    • 2642679375 scopus 로고    scopus 로고
    • note
    • Other methods for the enolate oxidation of 20 were briefly examined. Examples include deprotonation with potassium hexamethyldisilazide and subsequent exposure of the enolate anion to oxygen or the Davis oxaziridine. However, subsequent sodium periodate oxidation in these cases proceeded in only 34% and 15% yield, respectively.
  • 34
    • 2642618711 scopus 로고    scopus 로고
    • note
    • 16 (equation presented)
  • 41
    • 0016849177 scopus 로고    scopus 로고
    • ref 7
    • For selected examples, see: (a) ref 7. (b) Masamune, S.; Yamamoto, H.; Kamata, S.; Fukuzawa, A. J. Am. Chem. Soc. 1975, 97, 3513. (c) Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3215.
  • 43
    • 0019440449 scopus 로고
    • For selected examples, see: (a) ref 7. (b) Masamune, S.; Yamamoto, H.; Kamata, S.; Fukuzawa, A. J. Am. Chem. Soc. 1975, 97, 3513. (c) Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3215.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3215
    • Woodward, R.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.