Total synthesis and stereochemical assignment of rakicidin F

Total synthesis of rakicidin F was accomplished in 20 linear steps (0.68% overall yield), which enabled the configural determination of its six stereogenic centers as 2 R , 15 R , 16 R , 17 S , 19 S , and 21 S . The macrolactonization of the rakicidin linear precursor was investigated and the unsucc...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 2; pp. 4135 - 414
Main Authors Han, Fangzhi, Liu, Guangju, Zhao, Xiuhe, Du, Shunshun, Ding, Yahui, Zhang, Quan, Deng, Huiting, Wang, Liang, Chen, Yue
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 26.05.2022
Subjects
Steric hindrance
Synthesis
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Summary:Total synthesis of rakicidin F was accomplished in 20 linear steps (0.68% overall yield), which enabled the configural determination of its six stereogenic centers as 2 R , 15 R , 16 R , 17 S , 19 S , and 21 S . The macrolactonization of the rakicidin linear precursor was investigated and the unsuccessful results might be attributed to the steric hindrance near C16-OH. Total synthesis of rakicidin F was accomplished and its unknown absolute configuration of stereogenic centers was confirmed.
Bibliography:https://doi.org/10.1039/d2ob00692h
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00692h