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IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins.

Publication ,  Journal Article
Fraser-Reid, B; Chen, XT; Haag, D; Henry, KJ; McPhail, AT
Published in: Chirality
June 2000

L-Rhamnal is readily converted into an allyl 2, 3-unsaturated-C-glycopyranoside. The (S) configuration of the alphaL-anomer defines the stereochemical outcome of the future IMDA reaction, leading to the absolute stereochemistry for the trans-decalin moiety in naturally occurring terpenoids. Selective cleavage of the terminal double bond of the allyl group provides an aldehydo function which serves for an aldol/Claisen addition with ethyl sorbate. Of the four possible diastereomers, one is obtained in pure form and processed to give the IMDA precursor. Cyclocondensation is achieved by heating in xylene to give a tricyclic trans-decalin whose structure is established by NMR and X-ray analysis.

Duke Scholars

Published In

Chirality

DOI

EISSN

1520-636X

ISSN

0899-0042

Publication Date

June 2000

Volume

12

Issue

5-6

Start / End Page

488 / 495

Related Subject Headings

  • X-Rays
  • Terpenes
  • Stereoisomerism
  • Organic Chemistry
  • Naphthalenes
  • Molecular Conformation
  • Models, Molecular
  • Models, Chemical
  • Magnetic Resonance Spectroscopy
  • Glycosides
 

Citation

APA
Chicago
ICMJE
MLA
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Fraser-Reid, B., Chen, X. T., Haag, D., Henry, K. J., & McPhail, A. T. (2000). IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins. Chirality, 12(5–6), 488–495. https://doi.org/10.1002/(sici)1520-636x(2000)12:5/6<488::aid-chir34>3.0.co;2-w
Fraser-Reid, B., X. T. Chen, D. Haag, K. J. Henry, and A. T. McPhail. “IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins.Chirality 12, no. 5–6 (June 2000): 488–95. https://doi.org/10.1002/(sici)1520-636x(2000)12:5/6<488::aid-chir34>3.0.co;2-w.
Fraser-Reid B, Chen XT, Haag D, Henry KJ, McPhail AT. IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins. Chirality. 2000 Jun;12(5–6):488–95.
Fraser-Reid, B., et al. “IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins.Chirality, vol. 12, no. 5–6, June 2000, pp. 488–95. Epmc, doi:10.1002/(sici)1520-636x(2000)12:5/6<488::aid-chir34>3.0.co;2-w.
Fraser-Reid B, Chen XT, Haag D, Henry KJ, McPhail AT. IMDA/aldol strategy for transforming carbohydrates into functionalized trans-decalins. Chirality. 2000 Jun;12(5–6):488–495.
Journal cover image

Published In

Chirality

DOI

EISSN

1520-636X

ISSN

0899-0042

Publication Date

June 2000

Volume

12

Issue

5-6

Start / End Page

488 / 495

Related Subject Headings

  • X-Rays
  • Terpenes
  • Stereoisomerism
  • Organic Chemistry
  • Naphthalenes
  • Molecular Conformation
  • Models, Molecular
  • Models, Chemical
  • Magnetic Resonance Spectroscopy
  • Glycosides