Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D |
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Authors: | Reddy P Ganapati Varghese Babu Baskaran Sundarababu |
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Institution: | Department of Chemistry, Indian Institute of Technology, Madras, Chennai-600036, India. |
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Abstract: | reaction: see text] A novel and general method for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide initiated electrophilic cyclization of azides has been developed and applied in the synthesis of (+/-)-indolizidine 167B and 209D with an overall yield of 16.5% and 17.8%, respectively. The efficiency of this methodology is further exemplified in the synthesis of azepine skeleton via tandem cation-olefin-azide cyclization. |
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