Asymmetric Synthesis of (-)- Pterosin N from a Chiral 1,3-Dioxolanone

作者：Wu Hsiu Han; Hsu Shao Chien; Hsu Feng Lin; Uang Biing Jiun^*

来源：European Journal of Organic Chemistry, 2014, 2014(20): 4351-4355.

DOI：10.1002/ejoc.201402234

• Natural products
• Total synthesis
• Asymmetric synthesis
• Diels-Alder reactions
• Synthetic methods

The first asymmetric total synthesis of (-)-pterosin N from the N, N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8% overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a dieneynone by Stille coupling, and an intramolecular Diels-Alder reaction followed by aromatization to finish the synthesis.

• 出版日期2014-7
• 单位清华大学