Abstract:The
first total syntheses of two 4,10-dihydroxy-8,12-guaianolides
that were reported to be natural products were achieved. Toward the
syntheses of a collection of related guaianolides, the typical 5,7-fused
system of 8,12-guaianolides was constructed by a ring expansion reaction
of a hydroxylated coronafacic acid analogue that can be practically
synthesized and optically resolved. The total syntheses of these compounds
revealed that the previously reported structures of both natural products
were incorrect.
“…8,12-Guaianolides are a less represented class though a few new molecules have been isolated recently. 57 (+)-Mikanokryptin 126 (Fig. 4) belonging to this class has been synthesized recently by Maimone and co-workers 58 in 2017 based on intermolecular and intramolecular double Barbier-type allylation for central 7-membered ring formation (Scheme 16).…”
Section: Synthesis Of Guaianolide Lactonesmentioning
Sesquiterpene lactones specially the guaianolides representing a bigger class of natural products have served as appealing candidates for total synthesis due to their varied bio- and pharmaceutical activities. This tutorial...
“…8,12-Guaianolides are a less represented class though a few new molecules have been isolated recently. 57 (+)-Mikanokryptin 126 (Fig. 4) belonging to this class has been synthesized recently by Maimone and co-workers 58 in 2017 based on intermolecular and intramolecular double Barbier-type allylation for central 7-membered ring formation (Scheme 16).…”
Section: Synthesis Of Guaianolide Lactonesmentioning
Sesquiterpene lactones specially the guaianolides representing a bigger class of natural products have served as appealing candidates for total synthesis due to their varied bio- and pharmaceutical activities. This tutorial...
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