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Volumn 42, Issue 22, 2001, Pages 3673-3675

An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one: A formal synthesis of (±)-mesembranol

Author keywords

[No Author keywords available]

Indexed keywords

4 (TERT BUTYLDIMETHYLSILYLOXY)CYCLOHEX 2 EN 1 ONE; HYDROXYL GROUP; KETONE DERIVATIVE; LIMONENE; LIMONENE OXIDE; MESEMBRANOL; TRIFLUOROMETHANESULFONIC ACID VINYL ESTER; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0035962985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)00481-6     Document Type: Article
Times cited : (32)

References (21)
  • 7
    • 0342847839 scopus 로고    scopus 로고
    • Both (R)- and (S)-limonene oxide is commercially available, normally at equal cost, allowing an effective means of preparing either enantiomer of 2a
    • Both (R)- and (S)-limonene oxide is commercially available, normally at equal cost, allowing an effective means of preparing either enantiomer of 2a.
  • 11
    • 33751392466 scopus 로고
    • Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454. No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363-2366, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate.
    • (1992) J. Org. Chem. , vol.57 , pp. 3454
    • Cane, D.E.1    Yang, G.2    Coates, R.M.3    Pyun, H.4    Hohn, T.M.5
  • 12
    • 0000083470 scopus 로고
    • No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate
    • Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454. No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363-2366, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2363-2366
    • Schreiber, S.L.1    Liew, W.F.2
  • 14
    • 0343282526 scopus 로고    scopus 로고
    • Without careful removal of the palladium catalyst, distillation of the diene results in aromatization to toluene. However, 20 g of product can be filtered through 1/2 inch of silica, eluting with hexane.
    • Without careful removal of the palladium catalyst, distillation of the diene results in aromatization to toluene. However, 20 g of product can be filtered through 1/2 inch of silica, eluting with hexane.
  • 16
    • 0024588558 scopus 로고
    • On a larger scale, 2a can be distilled (>90% purity by GC)
    • On a larger scale, 2a can be distilled (>90% purity by GC). Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2599
    • Danishefsky, S.J.1    Simoneau, B.2
  • 17
    • 0343718026 scopus 로고    scopus 로고
    • note
    • 4, and concentrated. Flash chromatography (4:1 hex-EtOAc) afforded 10.4 g (83%) of a clear colorless oil.
  • 18
    • 0343282528 scopus 로고    scopus 로고
    • Racemic 2a was synthesized as a standard for HPLC analysis. The ee was determined by HPLC: ChiralCel OD 25 cm with 5 cm guard column (97:3, hexane:i-PrOH, 1 mL/min), (S)-enantiomer 6.1 min, (R)-enantiomer 6.7 min. (R)-Limonene oxide, purchased from Aldrich is reported as 98.5% ee.
    • Racemic 2a was synthesized as a standard for HPLC analysis. The ee was determined by HPLC: ChiralCel OD 25 cm with 5 cm guard column (97:3, hexane:i-PrOH, 1 mL/min), (S)-enantiomer 6.1 min, (R)-enantiomer 6.7 min. (R)-Limonene oxide, purchased from Aldrich is reported as 98.5% ee.
  • 19
    • 0343718027 scopus 로고    scopus 로고
    • Enone 2b was used in racemic form.
    • Enone 2b was used in racemic form.
  • 21
    • 0342847838 scopus 로고    scopus 로고
    • 3 in contrast yields the complimentary 1,5-reduction adduct 12.
    • 3 in contrast yields the complimentary 1,5-reduction adduct 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.