Stereoselective total synthesis of natural product crisamicin A (1) was accomplished for the first time via the Pd/TMTU-catalyzed alkoxycarbonylative annulation to generate a unique cis-pyran-fused lactone, an intermolecular Diels-Alder reaction to construct the pyranonaphthoquinone unit, and a novel Pd-thiourea pincer complex-catalyzed homocoupling of functionalized naphthoquinones.
Diversity-Oriented Synthesis of Fused Pyran γ-Lactones via an Efficient Pd−Thiourea-Catalyzed Alkoxycarbonylative Annulation
作者:Zhengtao Li、Yingxiang Gao、Zhaodong Jiao、Na Wu、David Zhigang Wang、Zhen Yang
DOI:10.1021/ol802115u
日期:2008.11.20
We reported herein a diversity-oriented synthesis of a range of fused pyran-gamma-lactones that was effected through a versatile Pd-thiourea complex-catalyzed intramolecular alkoxycarbonylative annulation.