Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02094
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Funding
- SERB New Delhi
- CSIR
- [CRG/2021/000427]
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In this study, an efficient diastereoselective allylation of aldehydes with functionalized allyl bromolactone was utilized to achieve the protecting-group-free divergent total synthesis of various guaianolides (+)-ligustrin, (+)-8-epi-ligustrin, and (+)-grosheimin, as well as the formal synthesis of (-)-eupalinilide E.
An efficient diastereoselective allylation of aldehydes with functionalized allyl bromolactone paved an excellent path toward the protecting-group-free divergent total synthesis of various guaianolides (+)-ligustrin, (+)-8-epi-ligustrin, and (+)-grosheimin and the formal synthesis of (-)-eupalinilide E. The key steps include diastereoselective allylation, efficient translactonization, and aldehyde-ene reaction. From the common intermediate molecule (+)-ligustrin, the first asymmetric total synthesis of (+)-grosheimin has been achieved.
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