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Novel Strategies for the Construction of Complex Polycyclic Ether Frameworks. Stereocontrolled Synthesis of the FGHIJ Ring System of Brevetoxin A

✍ Scribed by K. C. Nicolaou; C. A. Veale; C.-K. Hwang; J. Hutchinson; C. V. C. Prasad; W. W. Ogilvie


Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
553 KB
Volume
30
Category
Article
ISSN
0044-8249

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The substituted dioxacyclic compounds (III) and (XI) are synthesized via the inter-and intramolecular "pincer" Diels-Alder reaction. The first ring-opening reaction of these compounds is significantly faster than the second. Treatment of tetracycle (IV) with BuLi at higher temperatures provides the