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Issue 31, 2019
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Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

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Abstract

A concise total synthesis of seminolipid, a sulfoglycolipid, has been achieved; key features include regioselective, tin-free sulfation of allyl β-D-galactopyranoside using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent, stereoselective epoxidation, and site-selective acylation. The utility of this divergent synthetic approach to introduce 2,2,2-trichloroethyl-protected sulfate group at an early stage without toxic and environmentally unfavorable tin reagents was demonstrated by the syntheses of three seminolipid analogues with different side-chains from the common intermediate.

Graphical abstract: Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

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Publication details

The article was received on 27 Jun 2019, accepted on 23 Jul 2019 and first published on 24 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01445D
Org. Biomol. Chem., 2019,17, 7325-7329

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    Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

    N. Shimada, K. Fukuhara, S. Urata and K. Makino, Org. Biomol. Chem., 2019, 17, 7325
    DOI: 10.1039/C9OB01445D

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