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Synthetic studies toward ryanodol, ryanodine, and related insecticidal natural products

Reisman, Sarah (2018) Synthetic studies toward ryanodol, ryanodine, and related insecticidal natural products. In: 256th American Chemical Society National Meeting & Exposition, 19-23 August 2018, Boston, MA.

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(+)-Ryanodine was first identified in 1948 by Folkers and coworkers as part of an effort to identify the insecticidal constituents of Ryania speciosa Vahl, a shrub native to Central and South America. In fact, the crude ext. from the shrub was marketed as Ryanex, a non-specific insecticide. However, this product was later removed from the market and efforts to make improved ryanodine-derived insecticides have been thwarted by challenging synthetic chem. In this seminar, we will describe a synthetic strategy that provides access to (+)-ryanodine and the related natural product (+)- 20-deoxyspiganthine in 18 and 19 steps, resp. A key feature of this strategy is the reductive cyclization of an epoxide intermediate that possesses the crit. pyrrole-2-carboxylate ester. We will also describe recent efforts to prep. the antifeedant isoryanoid natural product perseanol.

Item Type:Conference or Workshop Item (Paper)
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Reisman, Sarah0000-0001-8244-9300
Additional Information:© 2018 American Chemical Society.
Record Number:CaltechAUTHORS:20181101-132923115
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:90577
Deposited By: Tony Diaz
Deposited On:01 Nov 2018 21:06
Last Modified:03 Oct 2019 20:26

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