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Volumn 43, Issue 36, 2002, Pages 6373-6376

A short synthesis of the C15-C21 segment of (+)-discodermolide, based on an asymmetric approach from achiral 2-methyl-1,3-propanediol to versatile enantiopure stereotriads

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 1,3 PROPANEDIOL DIOCTANOATE; ALDEHYDE; BROMINE DERIVATIVE; DISCODERMOLIDE; OXAZABOROLIDINE DERIVATIVE; PROPANEDIOL DERIVATIVE; SILICON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037009708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01373-4     Document Type: Article
Times cited : (18)

References (28)
  • 15
    • 0027380737 scopus 로고
    • . The Weinreb ester of 2,3-syn-3,4-anti isomer was obtained via a double differential, asymmetric aldol reaction of a chiral aldehyde with a chiral Evans' nucleophile in ∼50% yield over five steps, according to a similar procedure of Heathcock, see: Clark D.L., Heathcock C.H. J. Org. Chem. 58:1993;5878.
    • (1993) J. Org. Chem. , vol.58 , pp. 5878
    • Clark, D.L.1    Heathcock, C.H.2
  • 16
    • 0011073454 scopus 로고    scopus 로고
    • 2-Methyl-1,3-propanediol was purchased from Aldrich (1 L, ¥ 4.100; 2000-2001 catalog).
    • 2-Methyl-1,3-propanediol was purchased from Aldrich (1 L, ¥ 4.100; 2000-2001 catalog).
  • 17
    • 0011150736 scopus 로고    scopus 로고
    • The silylketene acetal 4 (Z:E=3:1), which accompanies the corresponding C-silyl ester, by trapping the lithium enolate with TMSOTf.
    • The silylketene acetal 4 (Z:E=3:1), which accompanies the corresponding C-silyl ester, by trapping the lithium enolate with TMSOTf.
  • 21
    • 0011132948 scopus 로고    scopus 로고
    • The stereochemistry of 7 was confirmed by J values and NOE measurements of 11 and 12.
    • The stereochemistry of 7 was confirmed by J values and NOE measurements of 11 and 12.
  • 23
    • 0011105628 scopus 로고    scopus 로고
    • The stereochemistry of 15 was determined by J values and NOE measurements of 16.
    • The stereochemistry of 15 was determined by J values and NOE measurements of 16.
  • 25
    • 0011070346 scopus 로고    scopus 로고
    • Even in the presence of non-protected β-OH, the chelation-controlled products can be predominantly obtained (Ref. 12).
    • Even in the presence of non-protected β-OH, the chelation-controlled products can be predominantly obtained ( Ref. 12 ).
  • 26
    • 0011102787 scopus 로고    scopus 로고
    • The stereochemistry of 17 was determined by J values and NOE measurements of 18.
    • The stereochemistry of 17 was determined by J values and NOE measurements of 18.
  • 27
    • 19044376917 scopus 로고    scopus 로고
    • . In a more simple system, the diastereoselective synthesis of 2,3-anti-3,4-anti and 2,3-anti-3,4-syn propionates has recently been reported by using a tandem sequence of Mukaiyama aldol reaction of α-methyl-β-protected-oxypropanal with a selenoenoxysilane and the following hydrogen transfer reaction: Guindon Y., Prévost M., Mochirian P., Guérin B. Org. Lett. 4:2002;1019.
    • (2002) Org. Lett. , vol.4 , pp. 1019
    • Guindon, Y.1    Prévost, M.2    Mochirian, P.3    Guérin, B.4
  • 28
    • 0011074329 scopus 로고    scopus 로고
    • note
    • 3, 100 MHz) δ (ppm) -5.4, -5.3, -4.1, -3.9, 10.4, 14.2, 14.4, 15.3, 18.3, 18.4, 26.0, 26.1, 38.6, 38.8, 44.8, 55.3, 60.2, 64.4, 74.4, 75.4, 81.8, 113.7, 129.0, 131.5, 159.1, 174.4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.