Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

Stereocontrolled synthesis of spirocyclics

Natural and synthetic 2H-pyran-2-ones and their versatility in organic synthesis☆

The chemistry of azadirachtin

The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks.

Synthesis of Chiral Cyclopentenones.

Ortho ester Claisen rearrangements of three 3-C-(hydroxymethyl)methylene derivatives of hexofuranose: stereoselective introduction of a quaternary center on C-3 of D-ribo-, L-lyxo-, and D-arabino-hexofuranoses

Stereoselective synthesis of the bis(tetrahydrofuran) moiety (C-1 to C-9) of (+)-asteltoxin, a novel mycotoxin from Aspergillus stellatus

Total synthesis of (+)-asteltoxin1

The ortho ester Claisen rearrangement of D-ribo- or L-lyxo- hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product. The stereochemistry of a newly introduced quaternary center of the product was unambiguously established by a chemical modification.

Introduction of gem-dialkyl group to hexofuranose by ortho ester Claisen rearrangement.

Claisen rearrangement of (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-.alpha.-D-ribo-hexofuranose with triethyl orthopropionate

Hirohiko Yamada

Papers

Ortho ester Claisen rearrangements of three 3-C-(hydroxymethyl)methylene derivatives of hexofuranose: stereoselective introduction of a quaternary center on C-3 of D-ribo-, L-lyxo-, and D-arabino-hexofuranoses

Stereoselective synthesis of the bis(tetrahydrofuran) moiety (C-1 to C-9) of (+)-asteltoxin, a novel mycotoxin from Aspergillus stellatus

Total synthesis of (+)-asteltoxin1

Introduction of gem-dialkyl group to hexofuranose by ortho ester Claisen rearrangement.

Claisen rearrangement of (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-.alpha.-D-ribo-hexofuranose with triethyl orthopropionate