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
NLM
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.
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