By Thilo J. Heckrodt, Johann Mulzer (auth.), Johann Mulzer (eds.)
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Extra resources for Natural Products Synthesis II: Targets, Methods, Concepts
15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 39. 40. 41. 42. 43. 44. 45. Marine Natural Products from Pseudopterogorgia elisabethae 41 46. Harrowven DC, Tyte MJ (2001) Tetrahedron Lett 42:8709 47. Chaplin JH, Edwards AJ, Flynn BL (2003) Org Biomol Chem 1:1842 48. For a recent review on DA reactions, see Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis GE (2002) Angew Chem Int Ed 41:1668 and references therein. de 1 Introduction . . . .
10) reveals that an enophilic endo/exo 28 T. J. Heckrodt · J. Mulzer Scheme 16 Mulzer’s total synthesis of elisabethin A (22) attack from the top face (104, 105) shows strong steric interactions between the isobutenyl rest and the (E)-double bond of the diene unit. On the other hand, in the case of an endo bottom face attack (106), steric repulsion between the 19-methyl group and the (E)-double bond comes into play shifting the equilibrium to exo arrangement (107). These results make clear that unfunctionalized model systems are often not appropriate to predict stereochemical issues associated with IMDA cyclizations.
The above-mentioned strategy was validated by the synthesis of tetracycle 176 (Scheme 27). The required double diene 170 was prepared from 2,5-dimethoxytetrahydrofuran (168) by treating it with acid and the HWE reagent. 38 T. J. Heckrodt · J. Mulzer Scheme 26 Flynn’s retrosynthetic analysis of colombiasin A (36) Subsequent monosilylation and Wittig reaction furnished unsymmetrical double diene 170. The synthesis of the other Diels–Alder partner started from bromophenol 173 (prepared in three steps from dimethoxytoluene), which was doubly metalated and reacted with (S,S)-menthyl p-toluenesulfinate 173.