Asymmetric Total Synthesis of Ventilanones A and B, Two Naturally Occurring Pyranonaphthoquinones from Ventilago harmandiana
7
Issued Date
2022-07-01
Resource Type
ISSN
00397881
eISSN
1437210X
Scopus ID
2-s2.0-85128836620
Journal Title
Synthesis (Germany)
Volume
54
Issue
13
Start Page
3093
End Page
3104
Rights Holder(s)
SCOPUS
Bibliographic Citation
Synthesis (Germany) Vol.54 No.13 (2022) , 3093-3104
Suggested Citation
Deelertpaiboon P., Kongsriprapan S., Krajangsri S., Betterley N.M., Kuhakarn C., Reutrakul V. Asymmetric Total Synthesis of Ventilanones A and B, Two Naturally Occurring Pyranonaphthoquinones from Ventilago harmandiana. Synthesis (Germany) Vol.54 No.13 (2022) , 3093-3104. 3104. doi:10.1055/a-1773-4386 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/84182
Title
Asymmetric Total Synthesis of Ventilanones A and B, Two Naturally Occurring Pyranonaphthoquinones from Ventilago harmandiana
Author's Affiliation
Other Contributor(s)
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.