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Four-Step Total Synthesis of (+)-Yaoshanenolides A and B.

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 ?-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-(-)-?-phellandrene. The approach allows access to yaoshanenolides A and B in four linear steps in 11 and 13% overall yield.

SUBMITTER: Thorat SS

PROVIDER: S-EPMC6644681 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Four-Step Total Synthesis of (+)-Yaoshanenolides A and B.

Thorat Sagar S SS Palange Megha N MN Kontham Ravindar R

ACS omega 20180628 6

A highly concise bioinspired four-step total synthesis of yaoshanenolides A and B possessing tricyclic spirolactone with an unusual 5'<i>H</i>-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 γ-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(5<i>H</i>)-furanone ...[more]

PMID: 31458866

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