Strategies and Tactics in Organic Synthesis: Chapter 8. Exploring Prins Strategies for the Synthesis of Okilactomycin
- ISBN-10
- 0128056118
- ISBN-13
- 9780128056110
- Series
- Strategies and Tactics in Organic Synthesis
- Category
- Science
- Pages
- 344
- Language
- English
- Published
- 2013-07-29
- Publisher
- Elsevier Inc. Chapters
- Authors
- Jason M. Tenenbaum, William J. Morris, Daniel W. Custar
Description
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.
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- 2013-07-29
- 344 pages
- Ebook
- Elsevier Inc. Chapters
-
- 2013-07-29
- 344 pages
- Ebook
- Elsevier Inc. Chapters
-
- 2013-07-29
- 344 pages
- Ebook
- Elsevier Inc. Chapters
-
- 2013-07-29
- 344 pages
- Ebook
- Elsevier Inc. Chapters
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