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Development of a unified strategy for the syntheis of enmein-type ent-kauranoids

Beck, Jordan C. and Reisman, Sarah E. (2017) Development of a unified strategy for the syntheis of enmein-type ent-kauranoids. In: 253rd American Chemical Society National Meeting & Exposition, April 2-6, 2017, San Francisco, CA. https://resolver.caltech.edu/CaltechAUTHORS:20170502-080053912

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Abstract

Development of a unified strategy for the total synthesis of the enmein-type ent-Kauranoids is disclosed. A total synthesis campaign of this class of natural products is of particular interest due to the potent anti-proliferative activity of these natural products across a wide range of cancer cell lines. The synthetic strategy described relies upon formation of the central lactone unit through a challenging reductive crosselectrophile coupling reaction. This route is highly convergent, as it assembles the reductive coupling substrate through an esterification reaction of a stereochem.-rich epoxy alc. with a structurally complex [3.2.1|-bicyclooctane. The epoxy alc. can be assembled through a diastereoselective oxidn. sequence while the [3.2.1|-bicyclooctane can be prepd. through a gold-catalyzed Conia-ene reaction. The modularity of this synthesis can potentially provide access to a wide range of natural products with varying backbone functionalization. Current efforts directed toward the development of key reactions in this sequence and their application to the synthesis of these products will be presented.


Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription
https://www.acs.org/content/acs/en/meetings/spring-2017.htmlOrganizationConference Website
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2017 American Chemical Society.
Record Number:CaltechAUTHORS:20170502-080053912
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170502-080053912
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77116
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:02 May 2017 18:07
Last Modified:03 Oct 2019 17:53

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