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Total Syntheses of Furaquinocin A, B, and E
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2003-10-01 , DOI: 10.1021/ja0364118 Barry M. Trost 1 , Oliver R. Thiel 1 , Hon-Chung Tsui 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2003-10-01 , DOI: 10.1021/ja0364118 Barry M. Trost 1 , Oliver R. Thiel 1 , Hon-Chung Tsui 1
Affiliation
A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain via Horner-Wadsworth-Emmons reaction and assembly of the naphthoquinone with squaric acid based methodology leads to furaquinocin E. The use of differentially substituted squaric acid derivatives allows the synthesis of three analogues of furaquinocin E. The additional stereocenters in furaquinocin A and B can be introduced with a diastereoselective Sakurai allylation. The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B.
中文翻译:
呋喃喹啉 A、B 和 E 的全合成
使用交叉复分解或闭环复分解可以实现侧链的立体选择性延伸。获得的后期中间体成功转化为呋喃喹啉A和B。
更新日期:2003-10-01
中文翻译:
呋喃喹啉 A、B 和 E 的全合成
使用交叉复分解或闭环复分解可以实现侧链的立体选择性延伸。获得的后期中间体成功转化为呋喃喹啉A和B。