Marx John N, Ajlouni Abdulaziz
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA.
Nat Prod Commun. 2010 Jan;5(1):5-8.
The first synthesis of occidenol (1), a 4,5-dihydrooxipin-containing sesquiterpene, is reported. The stereochemistry is corrected from that postulated by Tomita and Hirose, by a synthesis starting with natural occidentalol (4), the stereochemistry of which was also initially in error. The route (schemes 1 and 2) utilizes a retro-electrocyclic [2+2+2] fragmentation with N2 expulsion from 9 to produce, quantitatively, the acid sensitive dihydrooxipin system.
据报道，首次合成了含有4,5-二氢氧杂䓬的倍半萜烯西地醇（1）。通过从天然西地醇（4）开始的合成对立体化学进行了修正，天然西地醇（4）的立体化学最初也是错误的，而富田和广濑所假定的立体化学是不正确的。该路线（方案1和方案2）利用了一种逆电环化[2+2+2]碎片化反应，从9中定量地排出N₂以生成对酸敏感的二氢氧杂䓬体系。
