Total Synthesis of Adunctin B

Total synthesis of (±)-adunctin B, a natural product isolated from <i>Piper aduncum</i> (Piperaceae), has been achieved using two different strategies, in seven and three steps. The efficient approach features highly atom economical and diastereoselective Friedel–Crafts acylation, alkylation reaction and palladium catalyzed Wacker type oxidative cyclization

Enantioselective Total Syntheses of (+)-Hostmanin A, (−)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel–Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (−)-linderol A. The synthetic and spectroscopic data investigations led to the structural reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis

Remarkable Switch of Regioselectivity in Diels–Alder Reaction: Divergent Total Synthesis of Borreverine, Caulindoles, and Flinderoles

Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products

Remarkable Switch of Regioselectivity in Diels–Alder Reaction: Divergent Total Synthesis of Borreverine, Caulindoles, and Flinderoles

Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products

Remarkable Switch of Regioselectivity in Diels–Alder Reaction: Divergent Total Synthesis of Borreverine, Caulindoles, and Flinderoles

Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products