Reddy, Ganapati P. ; Varghese, Babu ; Baskaran, Sundarababu (2003) 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 Organic Letters, 5 (4). pp. 583-585. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol027563v
Related URL: http://dx.doi.org/10.1021/ol027563v
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 98556 |
| Deposited On: | 19 Sep 2014 11:29 |
| Last Modified: | 19 Sep 2014 11:29 |
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