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DOI: 10.1055/a-1773-4386
Asymmetric Total Synthesis of Ventilanones A and B, Two Naturally Occurring Pyranonaphthoquinones from Ventilago harmandiana
We are grateful for the financial support from the NSRF through the Program Management Unit for Human Resources & Institutional Development, Research and Innovation [B16F640099], the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, and Mahidol University under the National Research Universities Initiative.
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Abstract
The asymmetric synthesis of the novel pyranonaphthoquinones ventilanone A and ventilanone B, isolated from the Thai endemic plant Ventilago harmandiana, is accomplished by employing l-rhamnose and gallic acid as the starting materials. The key reactions are the utilization of a newly introduced reagent, PhSCF2H/SnCl4, for the formylation of sterically hindered aromatics containing an electron-withdrawing methyl ester, and the efficient Hauser annulation of phenylthiophthalides with optically active C-1 glycals derived from l-rhamnose. The developed synthetic methodologies solve the long-standing problem of the formylation of sterically hindered aromatics containing electron-withdrawing groups, and are applicable for the synthesis of other analogues with substituents on the aromatic and pyran rings.
Key words
total synthesis - Hauser annulation - pyranonaphthoquinones - natural products - Ventilago harmandiana Pierre - ventilanonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1773-4386.
- Supporting Information
Publikationsverlauf
Eingereicht: 25. Januar 2022
Angenommen nach Revision: 16. Februar 2022
Accepted Manuscript online:
16. Februar 2022
Artikel online veröffentlicht:
07. April 2022
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