Details

Autor(en) / Beteiligte

• Li, Yong
• Chen, Zhi-Xing
• Xiao, Qing
• Ye, Qin-Da
• Sun, Tian-Wen
• Meng, Fan-Ke
• Ren, Wei-Wu
• You, Lin
• Xu, Ling-Min
• Wang, Yue-Fan
• Chen, Jia-Hua
• Yang, Zhen

Titel

Diastereoselective Total Synthesis of (±)-Schindilactone A, Part 2: Construction of the Fully Functionalized CDEFGH Ring System

Ist Teil von

• Chemistry, an Asian journal, 2012-10, Vol.7 (10), p.2334-2340

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2012

Quelle

Wiley Online Library Journals Frontfile Complete

Beschreibungen/Notizen

• The successful synthesis of the highly complex model compound (2) of the CEFGH ring system of schindilactone A (1) is described. Several synthetic methodologies were developed and applied to achieve this goal, including ring‐closing metathesis (RCM) and Co–thiourea‐catalyzed Pauson–Khand reactions. Furthermore, two independent approaches were developed for the construction of the GH ring of model compound 2, the key steps of which included Pd–thiourea‐catalyzed carbonylative annulation, methylation, and sequential RCM/oxa‐Michael‐addition reactions. The chemistry developed herein has provided a greater understanding of the synthesis of schindilactone A (1) and its analogous compounds of the same family. Two for the show: A highly complex model compound of the CEFGH ring system of schindilactone A (1) was synthesized. Key steps included Pd–thiourea‐catalyzed carbonylative annulation, methylation, and sequential RCM/oxa‐Michael‐addition reactions.