The first asymmetric total syntheses of both enantiomers of cryptocaryone

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• 作者：Hiromichi Fujioka ; Kenji Nakahara ; Tomohiro Oki ; Kie Hirano ; Tatsuya Hayashi ; Yasuyuki Kita
• 关键词：Cryptocaryone ; Chiral auxiliary ; Intramolecular bromoetherification ; CAN
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：14 April 2010
• 年：2010
• 卷：51
• 期：15
• 页码：1945-1946
• 全文大小：258 K

文摘

The first asymmetric total syntheses of the (+)- and (−)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butylammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1.