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Tetrahedron Letters
Volumn 34, Issue 43, 1993, Pages 6871-6874
Diastereoselective aldol reactions of β-silyloxy ethyl ketones. Application to the total synthesis of bafilomycin A1
Author keywords

[No Author keywords available]
Indexed keywords

BAFILOMYCIN A1;
EID: 0027383971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)91817-3     Document Type: Article
Times cited : (96)
References (18)
  • 7
    • 0026682593 scopus 로고
    • For another study which has addressed some of the synthetic challenges posed by this family of natural products see:
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3587-3590
    • Roush1    Bannister2
  • 9
    • 49949128203 scopus 로고
    • Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones
    • (1968) Tetrahedron Letters , pp. 2199-2204
    • Cherest1    Felkin2    Prudent3
  • 10
    • 0001078912 scopus 로고
    • Torsional strain involving partial bonds. The steric course of the reaction between allyl magnesium bromide and 4-t-butyl-cyclohexanone
    • (1968) Tetrahedron Letters , pp. 2205-2208
    • Cherest1    Felkin2    Prudent3
  • 14
    • 0003056540 scopus 로고
    • erythro-Selective aldol reaction using phenyldichloroborane.
    • 2 (1.3 equiv) and subsequent enolization (30 min −78, 30 min 0 °C). Subsequent aldol reactions were performed at −78 °C.
    • (1984) Chemistry Letters , pp. 1729-1732
    • Hamana1    Sasakura2    Sugasawa3
  • 15
    • 84918720630 scopus 로고    scopus 로고
    • The stereochemistry of the major adduct 7 was assigned by analogy. The stereochemistry of the minor adduct was not determined.
  • 16
    • 84918742800 scopus 로고    scopus 로고
    • 13C NMR spectral data was taken from reference 2b. The TLC, IR and optical rotations were performed on an authentic sample of the natural product.
  • 17
    • 84918740712 scopus 로고    scopus 로고
    • Calculations were performed using the MM3* force field and a montecarlo search routine within the BATCHMIN subprogram of MacroModel. For the enols from ketones 2 and 8, conformation A was ≈0.25 kcal/mole more stable than B. For the enol from ketone 6, conformation B was <0.1 kcal/mole more stable than A.
  • 18
    • 84918714039 scopus 로고    scopus 로고
    • 20 protons were also larger in 2 and 8 than in 6 (δ ppm: 0.22 for 2, 0.32 for 8, 0.09 for 6).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.