Asymmetric synthesis of methyl bacteriopheophorbide-d and analogues by stereoselective reduction of the 3-acetyl to the 3-(1-hydroxyethyl) group |
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| Institution: | 1. Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Higher Education District, Hangzhou 310018, PR China;2. State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China;1. Zavoisky Physical -Technical Institute of Kazan Scientific Center of Russian Academy of Sciences, Russian Federation;2. Arbuzov Organic and Physical Chemistry Institute of Kazan Scientific Center of Russian Academy of Sciences, Russian Federation |
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| Abstract: | Asymmetric borane-reduction of 3-acetyl-131-oxo-tetrapyrroles (=bacteriochlorin, chlorin and porphyrin) in the presence of a chiral source gave selectively chiral 3-(1-hydroxyethyl)-131-oxo-tetrapyrroles. Oxazaborolidines were effective as chiral auxiliaries. Reduction with (S)-oxazaborolidines led to the (31S)-alcohol as the major product, whose stereoselectivity was the opposite of that in the same asymmetric reduction of usual prochiral ketones ArCOR. The asymmetric reduction of the 3-acetyl group in methyl bacteriopyropheophorbide-a and the 7,8-oxidation afforded 31-epimeric methyl (31S)-bacteriopheophorbide-d (89% de). |
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