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Volumn 47, Issue 33, 2008, Pages 6189-6191

Total synthesis of the tetracyclic sesquiterpene (±)-punctaporonin C

Author keywords

Naturalproducts; Photochemistry; Regioselectivity; Terpenoids; Total synthesis

Indexed keywords

NATURALPRODUCTS; PHOTOCHEMISTRY; REGIOSELECTIVITY; TERPENOIDS; TOTAL SYNTHESIS;

EID: 51649086184     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801534     Document Type: Article
Times cited : (44)

References (41)
  • 5
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    • For (-)-punctaporonin A and (+)-punctoporonin D, see: T. Sugimura, L. A. Paquette, J. Am. Chem. Soc. 1986, 108, 3841-3842;
    • a) For (-)-punctaporonin A and (+)-punctoporonin D, see: T. Sugimura, L. A. Paquette, J. Am. Chem. Soc. 1986, 108, 3841-3842;
  • 9
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    • Eds, D. C. Neckers, D. H. Volman, G. Von Bünau
    • b) J.-P. Pete, Advances in Photochemistry, Vol. 21 (Eds.: D. C. Neckers, D. H. Volman, G. Von Bünau), 1996, pp. 135-216;
    • (1996) Advances in Photochemistry , vol.21 , pp. 135-216
    • Pete, J.-P.1
  • 17
    • 35348986501 scopus 로고    scopus 로고
    • For reviews on the use of photocycloaddition reactions in natural products synthesis, see: a
    • For reviews on the use of photocycloaddition reactions in natural products synthesis, see: a) J. Iriondo-Alberdi, M. F. Greaney, Eur. J. Org. Chem. 2007, 4801-4815;
    • (2007) Eur. J. Org. Chem , pp. 4801-4815
    • Iriondo-Alberdi, J.1    Greaney, M.F.2
  • 20
    • 0142183583 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 4824-4826;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4824-4826
  • 27
    • 0032510255 scopus 로고    scopus 로고
    • For examples in photochemistry of an increased steric demand of polar substituents through hydrogen bonding, see: a U. Lindemann, G. Reck, D. Wulff-Molder, P. Wessig, Tetrahedron 1998, 54, 2529-2544;
    • For examples in photochemistry of an increased steric demand of polar substituents through hydrogen bonding, see: a) U. Lindemann, G. Reck, D. Wulff-Molder, P. Wessig, Tetrahedron 1998, 54, 2529-2544;
  • 29
    • 0031024261 scopus 로고    scopus 로고
    • We have attempted to perform this reaction enantioselectively. The use of acetate as the nucleophile in the presence of a chiral Co-salen complex resulted in the formation of the product in 36% yield with 45% ee: a E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776;
    • We have attempted to perform this reaction enantioselectively. The use of acetate as the nucleophile in the presence of a chiral Co-salen complex resulted in the formation of the product in 36% yield with 45% ee: a) E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776;
  • 31
    • 33845679379 scopus 로고    scopus 로고
    • The more selective benzoate (up to 83% ee) is not compatible with the subsequent photocycloaddition
    • c) C. Schneider, Synthesis 2006, 3919-3944. The more selective benzoate (up to 83% ee) is not compatible with the subsequent photocycloaddition.
    • (2006) Synthesis , pp. 3919-3944
    • Schneider, C.1
  • 38
    • 33846495712 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 537-540.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 537-540
  • 40
    • 53549114662 scopus 로고    scopus 로고
    • The published 13C NMR spectroscopic data[1b] are shifted upfield consistently by 2 ppm as a result of a different calibration. In our experiments, D4]MeOH (δ, 49.1 ppm) was employed as an internal standard. We thank Prof. R. L. Edwards and Prof. D. J. Maitland for sharing this information with us
    • 4]MeOH (δ = 49.1 ppm) was employed as an internal standard. We thank Prof. R. L. Edwards and Prof. D. J. Maitland for sharing this information with us.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.