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Chapter 8. Exploring Prins Strategies for the Synthesis of Okilactomycin
出版Elsevier Inc. Chapters, 2013-07-29
主題Science / Chemistry / Organic
ISBN01280561189780128056110
URLhttp://books.google.com.hk/books?id=-CN3DAAAQBAJ&hl=&source=gbs_api
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註釋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.