Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.
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Jacobi et al. (1997) studied this question.
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