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used in many biomimetically-inspired syntheses of terpenes and steroids such as germanicol
(2.10) and progesterone (2.11) shown in Figure 2.6. 56,57
Figure 2.6 Natural products made by biomimetically-inspired syntheses.
Many variations of polyene cyclizations exist. However, a few themes occur in the
course of all these annulations. Cyclization initiation begins with the generation of a
carbocation. Various functional groups are used to generate a carbocation, such as sulfonate
esters, 58 acetals, 59 allylic alcohols, 60 epoxides, 56 and N-acyl iminiums. 61
Figure 2.7 Carbocation generation.
The methods of carbocation generation include protonation, solvolysis, or the
presence of a Lewis acid (Figure 2.7). Once the cation is generated, it undergoes an
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