Four-step total synthesis of (+)-yaoshanenolides A and B

TitleFour-step total synthesis of (+)-yaoshanenolides A and B
Publication TypeJournal Article
Year of Publication2018
AuthorsThorat, SS, Palange, MN, Kontham, R
JournalACS Omega
Volume3
Issue6
Pagination7036-7045
Date PublishedJUN
ISSN2470-1343
Abstract

A highly concise bioinspired four-step total synthesis of yaoshanenolides A and B possessing tricyclic spirolactone with an unusual 5'H-spiro-[bicyclo[2.2.2]-oct[2] ene-7,2'-furan]-5'-one scaffold is reported. This synthesis features high-yielding aldol-type addition of gamma-butyrolactone on to the aldehyde, exocyclic olefination of lactone derivative using Eschenmoser's salt, and highly facial-and endo-selective [4 + 2]-cycloaddition of fully functionalized 5-methylene-2(5H)-furanone with natural R-(-)-alpha-phellandrene. The approach allows access to yaoshanenolides A and B in four linear steps in 11 and 13% overall yield.

DOI10.1021/acsomega.8b00701
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)Not Available
Divison category: 
Organic Chemistry

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