IMDA/ALDOL strategy for transforming carbohydrates into functionalized trans-decalins

Chirality

Volumn 12, Issue 5-6, 2000, Pages 488-495

  Fraser Reid, Bert ^a   Chen, Xiao Tao ^b   Haag, Dieter ^a   Henry Jr , Kenneth J ^b   McPhail, Andrew T ^b  

^a Nat Prod Glycotechnology Res I   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

Azadirachtir; Halogen metal exchange; Unsaturated c glycosides; Z bromoglycals

Indexed keywords

AZADIRACHTIN; CARBOHYDRATE DERIVATIVE; DECALIN DERIVATIVE; GLYCOPYRANOSIDE; TERPENOID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; HEATING; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0034119135     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<488::AID-CHIR34>3.0.CO;2-W     Document Type: Article

References (33)

1. Fraser-Reid B, Anderson RC. Carbohydrate derivatives in the asymmetric synthesis of natural products. Progr Chem Organ Nat Products 1980;39:1-61.
2. Hanessian S. Total synthesis of natural products: the chiron approach. New York: Pergamon; 1983.
3. Lopez JC, Fraser-Reid B. Parlaying C-O chirality into C-C chirality: improving the cost/benefit ratio of carbohydrate templates. J Chem Soc Chem Commun 1997;2251-2257.
4. (a) Joulie MM, Wang PC, Semple JE. Total synthesis and revised structural assignment of (+)-Furanonycin. J Am Chem Soc 1980;102: 887-889.
5. (b) Aitken RA, Kilanyi SN. Asymmetric synthesis. Glasgow: Blackie Academic and Professional; 1992. p 31.
6. (a) Gomez AM, Lopez JC, Fraser-Reid B. Serial radical cyclization of pyranose-derived dienes in the stereocontrolled synthesis of Woodward's reserpine precursor. J Org Chem 1995;60:3859-3870.
7. (b) Lopez JC, Gomez AM, Fraser-Reid B. Serial radical reactions of glycals: ready routes to highly functionalized C-Glycosyl derivatives. J Org Chem 1995;60:3871-3878.
8. (c) Lopez JC, Gomez AM, Fraser-Reid B. Cyclization reactions of tethered radicals derived from 4-O-substituted-D-erythro-Octa-2,6-dieno-pyranosides. Stereoselective access to carbocycles and branched chain sugars. Aust J Chem 1995;48:333-352.
9. Rahman Md Abdur, Fraser-Reid B. Actinobolin via the anomeric effect. J Am Chem Soc 1985;107:5576-5578.
10. Fraser-Reid B, Tsang R. Carbocycles from carbohydrates: the "annulated sugar" approach. In: Lindberg T, editor. Strategies and tactics in organic synthesis, vol. 2. New York: Academic Press; 1989. p 123-162.
11. Primeau JL, Anderson RC, Fraser-Reid B. Annulated pyranosides: some cyclohexano and cyclopentano-sugars. J Am Chem Soc 1983;105: 5874-5879.
12. Taber DF. Intramolecular diels alder and alder ene reactions. Berlin: Springer; 1984.
13. Ziegler FE, Jaynes BH, Saindane MT. A synthetic route to forskolin. J Am Chem Soc 1987;109:8115-8116.
14. Somoza C, Darias J, Ruveda EA, Intramolecular Michael-Aldol condensation approach to the construction of advanced intermediates in the synthesis of forskolin. J Org Chem 1989;54:1539-1543.
15. Tsang R, Fraser-Reid B. Pyranose-enones provide ready access to functionalized trans-decalins via bis-annulated pyranosides obtained by intramolecular diels alder reactions. A key intermediate for forskolin. J Org Chem 1992;57:1065-1067.
16. Ley SV, Denholm AA, Wood A. The chemistry of azadirachtin. Natural Products Reports 1993:109-157.
17. Chemistry of insect antifeedants from azadirachta indica. Part 22. Functionalisation of the rearr decalin fragment of azadirachtin via a Claisen rearrangement reaction. Ley SV, Gutteridge CE, Pape AR, Spilling CD, Zumbrunn C. Synlett 1999;8:1295-1297. Synthesis and insect antifeedant activity of C-2 and C-5 substituted perhydrofurofurans and 3a-hydroxy-perhydrofurofurans. I. Gebbinck EAK, Bouwman CT, Bourgois M, Jansen BJM, de Groot A. Tetrahedron 1999;55:11051-11076. Synthetic studies on azadirachtin: construction of the highly functionalized rearr decalin moiety of azadirachtin. Ishihara J, Yamamoto Y, Kanoh N, Murai A. Tetrahedron Lett 1999;40:1907-1910. Synthetic studies on azadirachtin. 3. Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Ishihara J, Fukuzaki T, Murai A. Tetrahedron Lett 1999;40:1907-1910.
18. Chemistry of insect antifeedants from azadirachta indica. Part 22. Functionalisation of the rearr decalin fragment of azadirachtin via a Claisen rearrangement reaction. Ley SV, Gutteridge CE, Pape AR, Spilling CD, Zumbrunn C. Synlett 1999;8:1295-1297. Synthesis and insect antifeedant activity of C-2 and C-5 substituted perhydrofurofurans and 3a-hydroxy-perhydrofurofurans. I. Gebbinck EAK, Bouwman CT, Bourgois M, Jansen BJM, de Groot A. Tetrahedron 1999;55:11051-11076. Synthetic studies on azadirachtin: construction of the highly functionalized rearr decalin moiety of azadirachtin. Ishihara J, Yamamoto Y, Kanoh N, Murai A. Tetrahedron Lett 1999;40:1907-1910. Synthetic studies on azadirachtin. 3. Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Ishihara J, Fukuzaki T, Murai A. Tetrahedron Lett 1999;40:1907-1910.
19. Chemistry of insect antifeedants from azadirachta indica. Part 22. Functionalisation of the rearr decalin fragment of azadirachtin via a Claisen rearrangement reaction. Ley SV, Gutteridge CE, Pape AR, Spilling CD, Zumbrunn C. Synlett 1999;8:1295-1297. Synthesis and insect antifeedant activity of C-2 and C-5 substituted perhydrofurofurans and 3a-hydroxy-perhydrofurofurans. I. Gebbinck EAK, Bouwman CT, Bourgois M, Jansen BJM, de Groot A. Tetrahedron 1999;55:11051-11076. Synthetic studies on azadirachtin: construction of the highly functionalized rearr decalin moiety of azadirachtin. Ishihara J, Yamamoto Y, Kanoh N, Murai A. Tetrahedron Lett 1999;40:1907-1910. Synthetic studies on azadirachtin. 3. Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Ishihara J, Fukuzaki T, Murai A. Tetrahedron Lett 1999;40:1907-1910.
20. Chemistry of insect antifeedants from azadirachta indica. Part 22. Functionalisation of the rearr decalin fragment of azadirachtin via a Claisen rearrangement reaction. Ley SV, Gutteridge CE, Pape AR, Spilling CD, Zumbrunn C. Synlett 1999;8:1295-1297. Synthesis and insect antifeedant activity of C-2 and C-5 substituted perhydrofurofurans and 3a-hydroxy-perhydrofurofurans. I. Gebbinck EAK, Bouwman CT, Bourgois M, Jansen BJM, de Groot A. Tetrahedron 1999;55:11051-11076. Synthetic studies on azadirachtin: construction of the highly functionalized rearr decalin moiety of azadirachtin. Ishihara J, Yamamoto Y, Kanoh N, Murai A. Tetrahedron Lett 1999;40:1907-1910. Synthetic studies on azadirachtin. 3. Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Ishihara J, Fukuzaki T, Murai A. Tetrahedron Lett 1999;40:1907-1910.
21. Ferrier RJ, Prrasad N. Unsaturated carbohydrates. Part IX. Synthesis of 2,3-Dideoxy-α-D-erythro-hex-2-enopyranoside from Tri-O-acetyl-D-glucal. J Chem Soc C 1969;570-591.
22. Danishefsky SJ, Kerwin JF Jr. On the addition of allyltrimethylsilane to glycal acetates. J Org Chem 1982;47:3803-3805.
23. (a) Fogh A, Lundt I, Pedersen C, Rasmussen P. Preparation of some 2-bromo-2-deoxy-D-hexopyranoses. Acta Chem Scand 1977;B31:768-770.
24. (b) Hayashi M, Amano K, Tsukada K, Lamberth C. Efficient synthesis of unsaturated branched-chain sugars in aqueous media by heck-type reaction. J Chem Soc Perkin Trans I 1999;239-240.
25. Lemieux RU, Fraser-Reid B. The bromination and halogenomethoxylation of D-glucal triacetate. Can J Chem 1964;42:532-538.
26. Lemieux RU, Lineback DR. The mechanism of the dehydrobromination of tetra-O-Acetyl-α-D-Glucopyranosyl Bromide. Can J Chem 1965; 43:94-105.
27. Collins P, Ferrier R. Monosaccharides. New York: Wiley & Sons; 1995. p 539.
28. Pappo R, Allen DS, Lemieux RU, Johnson WS. Osmium tetroxide-catalyzed periodate oxidation of olefinic bonds. J Org Chem 1956;21: 478-479.
29. Lopez JC, Gomez AM, Fraser-Reid B. Silicon tethered radical cyclization with IMDA strategies are combined to provide a ready rearr route highly functionalized decalins. J Chem Soc Chem Commun 1993;762-764.
30. Johnson CK. ORTEPII: report ORNL-5138. Oakridge, TN: Oak Ridge National Laboratory; 1986.
31. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AIG, Taylor R. Tables of bond lengths determined by x-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J Chem Soc Perkin Trans II 1987;S1:.
32. Frenz BA, and Associates Inc. SDP3.0: structure determination package. College Station, Texas, and Enraf-Nonius, Delft, The Netherlands; 1985.
33. Ibers JA, Hamilton WC. International tables for x-ray crystallography, Kynoch, vol. 4. Birmingham, UK; 1974.