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Unified total syntheses of (±)-sessilifoliamides B, C, and D
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Olivier, WJ 
ORCID: 0000-0002-8838-9609, Bissember, AC ORCID: 0000-0001-5515-2878 and Smith, JA ORCID: 0000-0001-6313-3298 2021
, 'Unified total syntheses of (±)-sessilifoliamides B, C, and D'
, Organic Letters, vol. 23, no. 9
, pp. 3437-3441
, doi: 10.1021/acs.orglett.1c00895.
ORCID: 0000-0002-8838-9609, Bissember, AC ORCID: 0000-0001-5515-2878 and Smith, JA ORCID: 0000-0001-6313-3298 2021
, 'Unified total syntheses of (±)-sessilifoliamides B, C, and D'
, Organic Letters, vol. 23, no. 9
, pp. 3437-3441
, doi: 10.1021/acs.orglett.1c00895.
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Abstract
The first total syntheses of the Stemona alkaloids sessilifoliamides B and D and the second synthesis of sessilifoliamide C have been completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Brønsted acid mediated cyclization and controlled oxidation with Dess–Martin periodinane. This delivered sessilifoliamide C (and its C-11 epimer) in 24% yield over 11 steps, and sessilifoliamides B and D in 13 and 17 steps, respectively.
| Item Type: | Article |
|---|---|
| Authors/Creators: | Olivier, WJ and Bissember, AC and Smith, JA |
| Keywords: | Stemona, sessilifoliamide, polycyclic alkaloids, lactam |
| Journal or Publication Title: | Organic Letters |
| Publisher: | Amer Chemical Soc |
| ISSN: | 1523-7060 |
| DOI / ID Number: | 10.1021/acs.orglett.1c00895 |
| Copyright Information: | Copyright 2021 American Chemical Society |
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| Item Statistics: | View statistics for this item |
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