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Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement
Alternative TitleSynthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement
Yang L(杨林)1; He GL(和国力)1; Yin RF(银瑞峰)1; Zhu LL(朱莉莉)1; Wang XX(王小霞)1; Hong R(洪然)1
2014
Source PublicationAngew. Chem.-Int. Edit.
Volume53Issue:43Pages:11600-11604
AbstractPolyketide antibiotics bearing skipped polyols represent a synthetic challenge. A SiCl4-promoted oxonia-Cope rearrangement of syn,syn-2-vinyl-1,3-diols was developed to forge an array of 1,5-pentenediols, thus providing versatile motifs for the preparation of 1,2,3,5-stereoarrays in a highly stereoselective manner. Further exploration with Sn(OTf)(2) realized the rearrangement of a cross-aldehyde which tactically warrants the utility of the current approach to access complex polyketides. The origin of high stereoselectivity is attributed to a chairlike anti-conformation of the oxonium ion intermediate.
Subject Area天然产物有机化学
DOI10.1002/anie.201407231
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Indexed BySCI
Language英语
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38991
Collection中科院天然产物有机化学重点实验室
Corresponding AuthorHong R(洪然)
Affiliation1.中科院上海有机化学研究所
2.浙江师范大学
Recommended Citation
GB/T 7714
Yang L,He GL,Yin RF,et al. Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement[J]. Angew. Chem.-Int. Edit.,2014,53(43):11600-11604.
APA 杨林,和国力,银瑞峰,朱莉莉,王小霞,&洪然.(2014).Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement.Angew. Chem.-Int. Edit.,53(43),11600-11604.
MLA 杨林,et al."Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement".Angew. Chem.-Int. Edit. 53.43(2014):11600-11604.
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