Total Synthesis and Structure Revision of Diplobifuranylone B
Total Synthesis and Structure Revision of Diplobifuranylone B
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DOI：
10.1021/acs.joc.9b01613
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发表时间：
2019-09-06
影响因子：
3.6
通讯作者：
Zhang, Liming
中科院分区：
文献类型：
--
作者：
Cheng, Xinpeng;Quintanilla, Carlos D.;Zhang, Liming
以（R）-（+）-乳酸甲酯和L-谷氨酸为起始原料，经10步不对称全合成双二呋喃酮B，总收率15.8%。该合成的特点是通过最近开发的不对称金催化在天然产物中立体选择性地构建关键的2，5-二氢呋喃环。由催化提供的立体化学灵活性使得能够对双二呋喃基酮B的报道结构进行有利的修正，其中2，5-二氢呋喃部分的相对立体化学先前被错误地指定为顺式而不是反式。
An asymmetric total synthesis of diplobifuranylone B was achieved in 10 steps for the longest linear sequence and in 15.8% overall yield from commercially available methyl (R)-(+)-lactate and L-glutamic acid. This synthesis features a stereoselective construction of the key 2,5-dihydrofuran ring in the natural product via a recently developed asymmetric gold catalysis. The stereochemical flexibility offered by the catalysis enables an expedient revision of the reported structure of diplobifuranylone B, where the relative stereochemistry of the 2,5-dihydrofuran moiety was previously misassigned as cis instead of trans.