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Synlett
DOI: 10.1055/a-2413-0587
letter

A concise asymmetric total synthesis of (+)-8-epigrosheimin via catalyst-free tandem allylboration-lactonization

Dhananjoy Maity
1   Biological & Synthetic Chemistry, Center of Biomedical Research, Lucknow, India (Ringgold ID: RIN371699)
2   Chemistry, University of Kalyani, Kalyani, India (Ringgold ID: RIN30132)
,
Ramkrishna Maity
1   Biological & Synthetic Chemistry, Center of Biomedical Research, Lucknow, India (Ringgold ID: RIN371699)
,
Manoranjan Jana 
3   Department of Chemistry, University of Kalyani, Kalyani, India (Ringgold ID: RIN30132)
3   Department of Chemistry, University of Kalyani, Kalyani, India (Ringgold ID: RIN30132)
,
Saumen Hajra 
4   Department Biological & Synthetic Chemistry, Center of Biomedical Research, Lucknow, India (Ringgold ID: RIN371699)
› Author AffiliationsSupported by: CSIR-EMR Grant CSIR-EMR grant (02(0398)/21/EMR-II)
Supported by: CBMR-IMR grant CBMR/IMR/0002/2021
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A concise and scalable asymmetric synthesis of (+)-8-epigroshimine is reported in 9 steps using only 3 column chromatographic purifications with an overall yield 47.0% from (R)-(-) carvone. Two synthetic routes are evaluated by catalyst-free tandem allylboration-lactonization of two carvone-derived aldehydes and subsequent ene-cyclization, where strategy via Lee-Lay aldehyde is found to be more effective for 8-epigrosheimin.



Publication History

Received: 09 August 2024

Accepted after revision: 10 September 2024

Accepted Manuscript online:
10 September 2024

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