Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones

A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed throug...

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Bibliographic Details
Published in:New journal of chemistry 2021-10, Vol.45 (4), p.18976-18982
Main Authors: Saini, Deepak, Kumar, Praveen, Fernandes, Rodney A
Format: Article
Language:English
Subjects:
Allyl compounds
Aspartic acid
Chemical reactions
Metathesis
Natural products
Stereoselectivity
Synthesis
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Summary:A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material, l -aspartic acid. Next, the allylation reaction was strategically utilized to provide the requisite olefin bond for the intended ring-closing metathesis, allowing the installation of the remaining dihydro-α-pyrone moiety in the natural products. It also enabled the targeting of both dihydro-α-pyrone diastereomers. Thus, the first stereoselective total synthesis of (+)-7′,8′-dihydroobolactone was accomplished, establishing its structure and absolute configuration. A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement and ring-closing metathesis.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj03990c