Progress toward a Convergent, Asymmetric Synthesis of Jervine

Progress toward a convergent approach for the enantioselective synthesis of the Veratrum alkaloid jervine is presented. The two requisite fragments were stereoselectively and efficiently fashioned from economical and readily available reagents. Key reactions include (a) a highly diastereoselective I...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (9), p.3537-3541
Main Authors: Zavesky, Blane P, De Jesús Cruz, Pedro, Johnson, Jeffrey S
Format: Article
Language:English
Subjects:
Chemistry Techniques, Synthetic - methods
Cyclization
Stereoisomerism
Veratrum Alkaloids - chemical synthesis
Veratrum Alkaloids - chemistry
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Summary:Progress toward a convergent approach for the enantioselective synthesis of the Veratrum alkaloid jervine is presented. The two requisite fragments were stereoselectively and efficiently fashioned from economical and readily available reagents. Key reactions include (a) a highly diastereoselective Ireland−Claisen rearrangement to establish the necessary cis-relationship between the amine and methyl group on the tetrahydrofuran E-ring; (b) a diastereoselective selenoetherification reaction that enabled the assembly of the D/E oxaspiro[4.5]­decene in the needed configuration; and (c) an enzymatic desymmetrization of an abundant achiral diol en route to a key four-carbon building block as a practical alternative to a protected Roche ester reduction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00972