Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B

Dawood, Rafid S.; Stockman, Robert A.

Abstract

A simple and efficient stereoselective total syntheses of two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields starting from a readily available alcohol is described. The key step in this synthetic route exploits the judicious use of solvent to enable a closed or open transition state in a nucleophilic addition of Grignard reagent to sulfinimine, giving selective access to two distinct diastereomers required for the formation of the two target natural products.

Citation

Dawood, R. S., & Stockman, R. A. (2021). Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B. European Journal of Organic Chemistry, 2021(27), 3850-3853. https://doi.org/10.1002/ejoc.202100453

• Journal Article Type: Article
• Acceptance Date: Jul 2, 2021
• Online Publication Date: Jul 21, 2021
• Publication Date: Jul 22, 2021
• Deposit Date: Aug 31, 2021
• Publicly Available Date: Jul 22, 2022
• Journal: European Journal of Organic Chemistry
• Print ISSN: 1434-193X
• Electronic ISSN: 1099-0690
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 2021
• Issue: 27
• Pages: 3850-3853
• DOI: https://doi.org/10.1002/ejoc.202100453
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/5817369
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100453
• Additional Information: This is the peer reviewed version of the following article: R. S. Dawood, R. A. Stockman, Eur. J. Org. Chem. 2021, 2021, 3850., which has been published in final form at https://doi.org/10.1002/ejoc.202100453. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.