Total synthesis and stereochemical assignment of rakicidin F

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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Veröffentlicht in:Organic & biomolecular chemistry 2022-05, Vol.2 (2), p.4135-414
Hauptverfasser: Han, Fangzhi, Liu, Guangju, Zhao, Xiuhe, Du, Shunshun, Ding, Yahui, Zhang, Quan, Deng, Huiting, Wang, Liang, Chen, Yue
Format: Artikel
Sprache:eng
Schlagworte:
Steric hindrance
Synthesis
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00692h