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Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B.

Publication ,  Journal Article
Kim, H; Baker, JB; Park, Y; Park, H-B; DeArmond, PD; Kim, SH; Fitzgerald, MC; Lee, D-S; Hong, J
Published in: Chemistry, an Asian journal
August 2010

Immunosuppressive drugs are used to prevent rejection of transplanted organs and treat autoimmune diseases. Clinically approved immunosuppressive drugs possess undesirable side effects, including acute neurological toxicity, chronic nephrotoxicity, and osteoporosis. As a result, considerable efforts have been devoted to the identification of immunosuppressive natural products that lack cytotoxicity and undesirable side effects on bone structure. Subglutinols A (1 a) and B (1 b) are diterpene pyrones isolated from Fusarium subglutinans. Compounds 1 a and 1 b are equipotent in the mixed lymphocyte reaction assay and thymocyte proliferation assay (IC(50) = 0.1 microM). Owing to the lack of toxicity, 1 a and 1 b are expected to be promising new immunosuppressive drugs. Herein, we detail our efforts that have culminated in a stereoselective synthesis of 1 a and 1 b from the (S)-(+)-5-methyl-Wieland-Miescher ketone and determined their absolute stereochemistries. We also present initial biological data to show the great potential of 1 a as an immunosuppressive drug with dose-dependent osteogenic activity.

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Published In

Chemistry, an Asian journal

DOI

EISSN

1861-471X

ISSN

1861-4728

Publication Date

August 2010

Volume

5

Issue

8

Start / End Page

1902 / 1910

Related Subject Headings

  • Structure-Activity Relationship
  • Stereoisomerism
  • Pyrones
  • Mice
  • Immunosuppressive Agents
  • General Chemistry
  • Fusarium
  • Diterpenes
  • Copper
  • Cell Line
 

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Kim, H., Baker, J. B., Park, Y., Park, H.-B., DeArmond, P. D., Kim, S. H., … Hong, J. (2010). Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B. Chemistry, an Asian Journal, 5(8), 1902–1910. https://doi.org/10.1002/asia.201000147
Kim, Hyoungsu, Joseph B. Baker, Yongho Park, Hyung-Bae Park, Patrick D. DeArmond, Seong Hwan Kim, Michael C. Fitzgerald, Dong-Sup Lee, and Jiyong Hong. “Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B.Chemistry, an Asian Journal 5, no. 8 (August 2010): 1902–10. https://doi.org/10.1002/asia.201000147.
Kim H, Baker JB, Park Y, Park H-B, DeArmond PD, Kim SH, et al. Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B. Chemistry, an Asian journal. 2010 Aug;5(8):1902–10.
Kim, Hyoungsu, et al. “Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B.Chemistry, an Asian Journal, vol. 5, no. 8, Aug. 2010, pp. 1902–10. Epmc, doi:10.1002/asia.201000147.
Kim H, Baker JB, Park Y, Park H-B, DeArmond PD, Kim SH, Fitzgerald MC, Lee D-S, Hong J. Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B. Chemistry, an Asian journal. 2010 Aug;5(8):1902–1910.
Journal cover image

Published In

Chemistry, an Asian journal

DOI

EISSN

1861-471X

ISSN

1861-4728

Publication Date

August 2010

Volume

5

Issue

8

Start / End Page

1902 / 1910

Related Subject Headings

  • Structure-Activity Relationship
  • Stereoisomerism
  • Pyrones
  • Mice
  • Immunosuppressive Agents
  • General Chemistry
  • Fusarium
  • Diterpenes
  • Copper
  • Cell Line