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Diastereoselective Total Synthesis of (±)‐Schindilactone A, Part 2: Construction of the Fully Functionalized CDEFGH Ring System
Author(s) -
Li Yong,
Chen ZhiXing,
Xiao Qing,
Ye QinDa,
Sun TianWen,
Meng FanKe,
Ren WeiWu,
You Lin,
Xu LingMin,
Wang YueFan,
Chen JiaHua,
Yang Zhen
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200364
Subject(s) - ring (chemistry) , total synthesis , stereochemistry , chemistry , organic chemistry
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.