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Volumn 8, Issue 18, 2006, Pages 3987-3990

De novo asymmetric synthesis of milbemycin β3 via an iterative asymmetric hydration approach

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; MILBEMYCIN;

EID: 33748931618     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061439k     Document Type: Article
Times cited : (36)

References (33)
  • 8
    • 33748932590 scopus 로고    scopus 로고
    • note
    • (a) Material Safety Data Sheet: Moxidectin: Fort Dodge Animal Health.
  • 10
    • 33748924945 scopus 로고    scopus 로고
    • Milbemycin class efflux pump inhibitors for treating microbial infections and cancer. WO 98-US20916 19981001, 1999 AN 1999:244572
    • Chamberland, S.; Lee, M.; Lomovskaya, O. Milbemycin class efflux pump inhibitors for treating microbial infections and cancer. WO 98-US20916 19981001, 1999 AN 1999:244572.
    • Chamberland, S.1    Lee, M.2    Lomovskaya, O.3
  • 22
    • 33748948821 scopus 로고    scopus 로고
    • note
    • 3 could be prepared from an achiral starting material, see: ref 8d.
  • 23
    • 33748928858 scopus 로고    scopus 로고
    • note
    • We prepared phosphine oxide 3 by a slightly modified variant of the Smith route, see Supporting Information and ref 7b.
  • 24
    • 85077634689 scopus 로고
    • Barrett had previously shown that the C-19 carboxylate could be installed by a Mitsunobu reaction, see: ref 7g and Mitsunobu, O. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 25
    • 0000417893 scopus 로고    scopus 로고
    • For examples of the asymmetric hydration of unsubstituted dienoates (e.g. 10 to 8), see: Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3(7), 1049-1052. Our study of the asymmetric hydration of substituted dienoates, will be published in due course.
    • (2001) Org. Lett. , vol.3 , Issue.7 , pp. 1049-1052
    • Hunter, T.J.1    O'Doherty, G.A.2
  • 29
    • 14844356105 scopus 로고    scopus 로고
    • Because most of the enantiomeric impurity in 7 is converted into the minor diastereomer ent-17b during the asymmetric dihydroxylation (7 to 17a/b), the major diastereomer diol 17a was isolated in essentially enantiomeric pure form. Consequently, the minor diastereomer I7b must be formed with lower enantiopurity. For other examples of this enantio-enriching phenomena, see: Ahmed, Md. M.; Berry, B. P.; Hunter, T. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745-748.
    • (2005) Org. Lett. , vol.7 , pp. 745-748
    • Ahmed, Md.M.1    Berry, B.P.2    Hunter, T.J.3    Tomcik, D.J.4    O'Doherty, G.A.5
  • 30
    • 33748938089 scopus 로고    scopus 로고
    • note
    • 2/hexane solvent mixture was critically important to ensure high yields for the palladium catalyzed reduction. For instance, use of THF as solvent gave a 1: 1 mixture of double bond regioisomers.
  • 33
    • 33748928048 scopus 로고    scopus 로고
    • note
    • 3 has been a source of disagreement. For an interesting discussion of this issue along with its resolution, see: ref 7 g.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.