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Unified total syntheses of (±)-sessilifoliamides B, C, and D

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.

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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
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Copyright 2021 American Chemical Society

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