Enantioselective Total Synthesis of Fortalpinoid Q via a TEMPO+BF4–-Mediated Dehydrative Nazarov Cyclization DOI

Hai-Kang Mao,

Qian Wang,

Jing Xu

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

The family of Cephalotaxus diterpenoids represents a captivating class natural products that are significant interest from both structural and biological perspectives within our community. Here we wish to report 15-step, enantioselective total synthesis the diterpenoid fortalpinoid Q. Our approach highlights (1) Jacobsen's catalytic Claisen rearrangement enabled single-step formation two vicinal stereogenic centers, including an all-carbon quaternary center; (2) mild, oxoammonium salt (TEMPO+BF4-)-promoted dehydrative Nazarov cyclization swiftly forged crucial cyclopentadiene moiety via unfunctionalized tertiary divinyl carbinol (TDC) substrate; (3) facile aldol-lactonization cascade ultimately resolved last obstacle in synthesis.

Language: Английский

Enantioselective Total Synthesis of Fortalpinoid Q via a TEMPO+BF4–-Mediated Dehydrative Nazarov Cyclization DOI

Hai-Kang Mao,

Qian Wang,

Jing Xu

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

The family of Cephalotaxus diterpenoids represents a captivating class natural products that are significant interest from both structural and biological perspectives within our community. Here we wish to report 15-step, enantioselective total synthesis the diterpenoid fortalpinoid Q. Our approach highlights (1) Jacobsen's catalytic Claisen rearrangement enabled single-step formation two vicinal stereogenic centers, including an all-carbon quaternary center; (2) mild, oxoammonium salt (TEMPO+BF4-)-promoted dehydrative Nazarov cyclization swiftly forged crucial cyclopentadiene moiety via unfunctionalized tertiary divinyl carbinol (TDC) substrate; (3) facile aldol-lactonization cascade ultimately resolved last obstacle in synthesis.

Language: Английский

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