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Updated: Jan 20, 2026
Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Four-Step Total Synthesis of (+)-Yaoshanenolides A and B
Sagar S Thorat1,2, Megha N Palange1,2, Ravindar Kontham1,2
1Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
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 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(5H)-furanone with natural R-(-)-α-phellandrene. The approach allows access to yaoshanenolides A and B in four linear steps in 11 and 13% overall yield.
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