REFERENCES

1. Barrett A, Ma T, Mies T. Recent developments in polyene cyclizations and their applications in natural product synthesis. Synthesis 2018;51:67-82.

2. Yoder RA, Johnston JN. A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids. Chem Rev 2005;105:4730-56.

3. Huff MW, Telford DE. Lord of the rings - the mechanism for oxidosqualene:lanosterol cyclase becomes crystal clear. Trends Pharmacol Sci 2005;26:335-40.

4. Harrison DM. The biosynthesis of triterpenoids and steroids. Nat Prod Rep 1985;2:525-60.

5. Thoma R, Schulz-Gasch T, D'Arcy B, et al. Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase. Nature 2004;432:118-22.

6. Woodward RB, Bloch K. The cyclization of squalene in cholesterol synthesis. J Am Chem Soc 1953;75:2023-4.

7. Stork G. The stereochemistry of polyene cyclization. Harvard University Organic colloquium Abstract. 1950. Burgstahler AW, PhD. Thesis. Harvard University: 1952.

8. Stork G, Burgstahler AW. The stereochemistry of polyene cyclization. J Am Chem Soc 1955;77:5068-77.

9. Eschenmoser A, Ruzicka L, Jeger O, Arigoni D. Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helv Chim Acta 1955;38:1890-904.

10. Eschenmoser A, Arigoni D. Revisited after 50 years: the “stereochemical interpretation of the biogenetic isoprene rule for the triterpenes”. HCA 2005;88:3011-50.

11. Corey EJ, Russey WE, Ortiz de Montellano PR. 2,3-Oxidosqualene, an intermediate in the biological synthesis of sterols from squalene. J Am Chem Soc 1966;88:4750-1.

12. Tamelen EE, Willett JD, Clayton RB, Lord KE. Enzymic conversion of squalene 2,3-oxide to lanosterol and cholesterol. J Am Chem Soc 1966;88:4752-4.

13. Cornforth JW. Olefin alkylation in biosynthesis. Angew Chem Int Ed Engl 1968;7:903-11.

14. Corey EJ, Virgil SC, Sarshar S. New mechanistic and stereochemical insights on the biosynthesis of sterols from 2,3-oxidosqualene. J Am Chem Soc 1991;113:8171-2.

15. Wendt KU, Schulz GE, Corey EJ, Liu DR. Enzyme mechanisms for polycyclic triterpene formation. Angew. Chem. Int. Edn Engl 2000; 39:2812-33.

16. Hérin M, Sandra P, Krief A. Stereospecific enzymic cyclization of a synthetic 2,3-oxidosqualene analogue bearing an 18Z carbon-carbon double bond. Tetrahedron Letters 1979;20:3103-6.

17. Krief A, Pasau P, Guittet E, Shan YY, Hérin M. Novel results on the biocyclisation of 2,3-oxidosqualene analogs by sterol cyclase. Bioorganic & Medicinal Chemistry Letters 1993;3:365-8.

18. Krief A, Schauder JR, Guittet E, Herve du Penhoat C, Lallemand JY. About the mechanism of sterol biosynthesis. J Am Chem Soc 1987;109:7910-1.

19. Hogeboom GH. Methods enzymol. Fractionation of cell components of animal tissues. Elsevier; 1955. p. 16-9.

20. Tamelen EE, Sharpless KB, Hanzlik R, Clayton RB, Burlingame AL, Wszolek PC. Enzymic cyclization of trans,trans,trans-18,19-dihydrosqualene 2,3-oxide. J Am Chem Soc 1967;89:7150-1.

21. Krief A, Pasau P, Quéré L. Comparison of the behavior of oxidosqualene cyclases from pig liver and yeast toward epoxy-squalene analogues possessing a Δ18-19 Z or E (C, C) double bond. Bioorganic & Medicinal Chemistry Letters 1991;1:365-8.

22. Krief A, Dunkle M, Bahar M, Bultinck P, Herrebout W, Sandra P. Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism. J Sep Sci 2015;38:2545-50.

23. Tamelen E, Sharpless KB. Positional selectivity during controlled oxidation of polyolefins. Tetrahedron Letters 1967;8:2655-9.

24. Krief A, Dumont W, Clarembeau M, Bernard G, Badaoui E. Synthesis of α-selenoalkyllithium compounds. Tetrahedron 1989;45:2005-22.

25. Labar D, Krief A. Connective (C-C) route to hindered epoxides and olefins from hindered ketones. J Chem Soc, Chem Commun 1982;10:564-6.

26. Horner L, Hoffmann H, Wippel HG, Klahre G. Phosphororganische Verbindungen, XX. Phosphinoxyde als Olefinierungsreagenzien. Chem Ber 1959;92:2499-505.

27. Buss AD, Warren S. The Wittig-Horner route to tri-substituted alkanes: synthesis of -α-bisabolene. Tetrahedron Letters 1983;24:111-4.

28. Schauder J, Krief A. Regio and stereochemically controlled ring opening of epoxides with Grignard reagents. Stereocontrolled synthesis of the steroid side chains. first stereoselective hemisynthesis of 20s isolanosterol. Tetrahedron Letters 1982;23:4389-92.

29. Koreeda M, Koizumi N. Stereochemically controlled synthesis of 20-isocholesterol. Tetrahedron Letters 1978;19:1641-4.

30. Pasau P. PhD thesis, Facultés Universitaires Notre-Dame de la Paix (FUNDP). Namur; 1992.

31. House HO, Gall M, Olmstead HD. Chemistry of carbanions. XIX. Alkylation of enolates from unsymmetrical ketones. J Org Chem 1971;36:2361-71.

32. Corey EJ, Suggs JW. Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Letters 1975;16:2647-50.

33. Evans DA, Truesdale LK, Grimm KG, Nesbitt SL. Thiosilanes, a promising class of reagents for selective carbonyl protection. J Am Chem Soc 1977;99:5009-17.

34. Barton DHR, Mccombie SW. A new method for the deoxygenation of secondary alcohols. J Chem Soc, Perkin Trans 1 1975; doi: 10.1039/p19750001574.

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