Exploring prins strategies for the synthesis of okilactomycin

Jason M. Tenenbaum, William J. Morris, Daniel W. Custar, Karl A. Scheidt*

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter

1 Scopus citations

Abstract

This account describes the convergent synthesis of (-)-okilactomycin. The first-generation approach focused on the assembly of two complex fragments through a Prins reaction of a dioxinone and α-hydroxy aldehyde. While this route was not ultimately successful, a related Maitland-Japp process employing a β-keto ester in place of the dioxinone fragment provided the necessary union of functionalized intermediate, thereby establishing the full carbon framework of the natural product. The synthesis also employed a highly diastereoselective Lewis acid-promoted Diels-Alder reaction and an olefin ring-closing metathesis to close the strained 11-membered macrocycle of the natural product.

Original languageEnglish (US)
Title of host publicationStrategies and Tactics in Organic Synthesis
PublisherAcademic Press Inc
Pages231-248
Number of pages18
ISBN (Print)9780080993621
DOIs
StatePublished - 2013

Publication series

NameStrategies and Tactics in Organic Synthesis
Volume9
ISSN (Print)1874-6004

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry

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    Tenenbaum, J. M., Morris, W. J., Custar, D. W., & Scheidt, K. A. (2013). Exploring prins strategies for the synthesis of okilactomycin. In Strategies and Tactics in Organic Synthesis (pp. 231-248). (Strategies and Tactics in Organic Synthesis; Vol. 9). Academic Press Inc. https://doi.org/10.1016/B978-0-08-099362-1.00008-4