Enantioselective Access to Decahydroquinolines Bearing a C4a or C8a Quaternary Stereocenter from a Common Intermediate Total Synthesis of (−)-Myrioxazine A DOI
Arnau Calbó,

Miriam Piccichè,

Llorenç Rubert

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 11, 2025

(R)-Phenylglycinol-derived perhydrooxazoloquinoline 2 provides stereoselective access to angularly substituted enantiopure decahydroquinolines (DHQs). Reaction of with appropriate Grignard reagents leads cis-DHQs bearing a C8a aza-quaternary stereocenter, whereas reaction Michael acceptors followed by reductive removal the 2-phenylethanol chiral inductor gives rise cis- or trans-DHQs C4a all-carbon quaternary stereocenter depending on hydride used for cleavage oxazolidine C-O bond. Theoretical studies have clarified mechanistic intricacies acceptors, providing arguments proper understanding observed stereoselectivity. Finally, formaldehyde is reversible, allowing regioselective formation either hydroxymethyl derivative 12 C8-substituted 13 temperature. An expeditious synthesis Myrioneuron-type alkaloid (-)-myrioxazine A from reported.

Язык: Английский

Enantioselective Access to Decahydroquinolines Bearing a C4a or C8a Quaternary Stereocenter from a Common Intermediate Total Synthesis of (−)-Myrioxazine A DOI
Arnau Calbó,

Miriam Piccichè,

Llorenç Rubert

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 11, 2025

(R)-Phenylglycinol-derived perhydrooxazoloquinoline 2 provides stereoselective access to angularly substituted enantiopure decahydroquinolines (DHQs). Reaction of with appropriate Grignard reagents leads cis-DHQs bearing a C8a aza-quaternary stereocenter, whereas reaction Michael acceptors followed by reductive removal the 2-phenylethanol chiral inductor gives rise cis- or trans-DHQs C4a all-carbon quaternary stereocenter depending on hydride used for cleavage oxazolidine C-O bond. Theoretical studies have clarified mechanistic intricacies acceptors, providing arguments proper understanding observed stereoselectivity. Finally, formaldehyde is reversible, allowing regioselective formation either hydroxymethyl derivative 12 C8-substituted 13 temperature. An expeditious synthesis Myrioneuron-type alkaloid (-)-myrioxazine A from reported.

Язык: Английский

Процитировано

0