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Synthesis of the 5-Hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Products Descurainin (Ia) and Cartorimine (Ib).

✍ Scribed by Barry B. Snider; James F. Grabowski

Publisher
John Wiley and Sons
Year
2006
Weight
11 KB
Volume
37
Category
Article
ISSN
0931-7597

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## Abstract The development and design of reliable and efficient methods for the construction of chiral building blocks are crucial in modern natural product synthesis. 8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐ones are readily accessible scaffolds with defined stereochemical features which have been exploited

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## Abstract Trichloro‐substituted 8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐ones **6** and **7** are solvolysed by methanolic sodium methoxide to form the bicyclo[3.2.1] α,α‐dimethoxy ketones **13** and **14**, with preservation of one chloro substituent. In the case of **6a**, prolonged reaction time with an