A Direct and Efficient Stereocontrolled Synthetic Route to the Pseudopterosins, Potent Marine Antiinflammatory Agents

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• 作者：E. J. Corey and Scott E. Lazerwith
• 刊名：Journal of the American Chemical Society
• 出版年：1998
• 出版时间：December 16, 1998
• 年：1998
• 卷：120
• 期：49
• 页码：12777 - 12782
• 全文大小：140K
• 年卷期：v.120,no.49(December 16, 1998)
• ISSN：1520-5126

文摘

Described herein is a new synthetic route to pseudopterosin aglycone (3), a key intermediate for thesynthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and E (2). Thepathway of synthesis starts with the abundant and inexpensive (S)-(-)-limonene and its long-known cyclichydroboration product (4) and leads to the chiral hydroxy ketone 6. Conversion of 6 to 10 followed by a novelaromatic annulation produced 15 which underwent a highly diastereoselective cyclization to afford the protectedpseudopterosin aglycone 16. The naturally occurring pseudopterosins such as 1 and 2 are readily availablefrom this key intermediate.