Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products,The Journal of Organic Chemistry

当前位置： X-MOL 学术 › J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acs.joc.7b02413
Hong-Shuang Wang ₁ , Hui-Jing Li ₁ , Xiang Nan ₁ , Yuan-Yuan Luo ₁ , Yan-Chao Wu _{1,

2}

Affiliation

An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork–Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.

中文翻译：

对苯二酚型海洋天然产物的对映体半合成

从香紫苏内酯仅7个步骤就可完成对映体半合成的puupehedione，总收率为25％。关键的drimanal三甲氧基苯乙烯骨架是通过芳基碘和drimanal hydr的钯催化交叉偶联反应构建的。原位CAN氧化/分子内oxa-Stork–Danheiser转座串联反应被用作一种强大的工具，可以一锅法同时安装puupehedione的C和D环。puupehenone和puupehenol的半合成也证明了其适用性。

更新日期：2017-11-08

点击分享查看原文

点击收藏

阅读更多本刊最新论文