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Volumn 6, Issue 1, 2011, Pages 209-219

Total synthesis of (-)-salinosporamide A

Author keywords

carbohydrates; inhibitors; natural products; rearrangement; total synthesis

Indexed keywords

BENZYL ESTERS; D-ARABINOSE; DEPROTECTION; FUNCTIONALIZATIONS; FUNCTIONALIZED; INHIBITORS; LACTAM STRUCTURE; LEWIS ACID; NATURAL PRODUCTS; ONE POT; OVERMAN REARRANGEMENT; PROTECTIVE GROUP; PYRANOSE; REARRANGEMENT; SALINOSPORAMIDE A; STEREO-SELECTIVE; STEREOCENTERS; TOTAL SYNTHESIS;

EID: 78650773335     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000602     Document Type: Article
Times cited : (29)

References (133)
  • 1
    • 0036855056 scopus 로고    scopus 로고
    • For selected recent reviews on proteasomes and their inhibitors, see J. Adams, Curr. Opin. Oncol. 2002, 14, 628-634
    • (2002) Curr. Opin. Oncol. , vol.14 , pp. 628-634
    • Adams, J.1
  • 7
    • 25144466132 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5944-5967
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5944-5967
  • 10
    • 0033022744 scopus 로고    scopus 로고
    • For selected reviews on natural products with γ-lactam-β- lactone structures, see E. J. Corey, W.-D. Z. Li, Chem. Pharm. Bull. 1999, 47, 1-10
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1-10
    • Corey, E.J.1    Li, W.-D.Z.2
  • 25
  • 29
  • 42
    • 78650767181 scopus 로고    scopus 로고
    • For total syntheses of omuralide (3), see ref.[6m]
    • For total syntheses of omuralide (3), see ref.[6m]
  • 45
  • 55
    • 78650778899 scopus 로고    scopus 로고
    • For TMC-95A-D as another type of proteasome inhibitors, see
    • For TMC-95A-D as another type of proteasome inhibitors, see
  • 60
  • 77
    • 51649114068 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6244-6246
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6244-6246
  • 90
    • 33847798567 scopus 로고
    • L. E. Overman, J. Am. Chem. Soc. 1976, 98, 2901-2910; for reviews on Overman rearrangements, see
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2901-2910
    • Overman, L.E.1
  • 93
    • 78650784065 scopus 로고    scopus 로고
    • See, refs.[6d], [6g], and [13f]
    • See, refs.[6d], [6g], and [13f]
  • 112
    • 70349765360 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 3799-3801.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3799-3801
  • 113
    • 78650781388 scopus 로고    scopus 로고
    • MacroModel 5.0, Schrödinger, Inc., Portland OR
    • MacroModel 5.0, Schrödinger, Inc., Portland OR
  • 115
    • 78650779505 scopus 로고    scopus 로고
    • Spartan 5.0.3, Wavefunction Inc., Irvine, CA
    • Spartan 5.0.3, Wavefunction Inc., Irvine, CA.
  • 118
    • 78650792519 scopus 로고    scopus 로고
    • The stereochemistry of 16 was determined by NOESY experiments. See the Supporting Information
    • The stereochemistry of 16 was determined by NOESY experiments. See the Supporting Information.
  • 119
    • 33847800833 scopus 로고
    • For a review on stereoselective methylation, see
    • For a review on stereoselective methylation, see:, E. C. Ashby, J. T. Laemmle, Chem. Rev. 1975, 75, 521-546.
    • (1975) Chem. Rev. , vol.75 , pp. 521-546
    • Ashby, E.C.1    Laemmle, J.T.2
  • 123
    • 78650762781 scopus 로고    scopus 로고
    • In the first-generation synthesis, PMB-protected trichloroimidate i underwent the Overman rearrangement with a similar stereoselectivity (ii/iii 4.3:1)
    • In the first-generation synthesis, PMB-protected trichloroimidate i underwent the Overman rearrangement with a similar stereoselectivity (ii/iii 4.3:1).
  • 124
    • 78650785338 scopus 로고    scopus 로고
    • The stereochemistry of 6 and 20 was determined by a NOESY experiment, see the Supporting Information
    • The stereochemistry of 6 and 20 was determined by a NOESY experiment, see the Supporting Information.
  • 125
    • 78650768765 scopus 로고    scopus 로고
    • Hemiaminal 6 existed as an equilibrium mixture of three compounds including the open chain aldehyde (6 / 6' / aldehyde 4:1:0.4), although the stereochemistry was not determined
    • Hemiaminal 6 existed as an equilibrium mixture of three compounds including the open chain aldehyde (6 / 6' / aldehyde 4:1:0.4), although the stereochemistry was not determined.
  • 126
    • 78650768177 scopus 로고    scopus 로고
    • 2O for 5d at 40°C did not give cyclic carbamate 25 and resulted in recovery of 6 in 91% yield. These results indicated that the cyclic carbamate was formed prior to formation of the aminal
    • 2O for 5d at 40°C did not give cyclic carbamate 25 and resulted in recovery of 6 in 91% yield. These results indicated that the cyclic carbamate was formed prior to formation of the aminal.
  • 127
    • 78650784727 scopus 로고    scopus 로고
    • Jones oxidation of primary alcohol 4 provided aldehyde 27, probably because the severe steric hindrance around the aldehyde carbonyl group prevented the formation of the large chromate ester
    • Jones oxidation of primary alcohol 4 provided aldehyde 27, probably because the severe steric hindrance around the aldehyde carbonyl group prevented the formation of the large chromate ester.
  • 128
    • 78650785134 scopus 로고    scopus 로고
    • Carboxylic acid 28 was the reported intermediate in the first-generation synthesis, see Ref.[13f]
    • Carboxylic acid 28 was the reported intermediate in the first-generation synthesis, see Ref.[13f].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.