ArticleThe Journal of organic chemistry2019
Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of Austalide Natural Products.
Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 23 citations in OpenAlex.
- Synthesis of Six Natural Products Enabled by Selective Hydroxylation of Orcinaldehyde-Like Substrates With an Enzyme Library.Angewandte Chemie (International ed. in English) · 2026Article
- Austalide derivative from marine-derivedRSC advances · 2023Article
- Marine Puupehenone and Puupehedione: Synthesis and Future Perspectives.Marine drugs · 2023Review
- Orthoester formation in fungal meroterpenoid austalide F biosynthesis.Philosophical transactions of the Royal Society of London. Series B, Biological sciences · 2023Article
- Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.Angewandte Chemie (International ed. in English) · 2019Article
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Authors and funding
3 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The first total synthesis of five austalide natural products, (±)-17 S-dihydroaustalide K, (±)-austalide K, (±)-13-deacetoxyaustalide I, (±)-austalide P, and (±)-13-deoxyaustalide Q acid, was accomplished via a series of biomimetic transformations. Key steps involved polyketide aromatization of a trans, trans-farnesol-derived β,δ-diketodioxinone into the corresponding β-resorcylate, followed by titanium(III)-mediated reductive radical cyclization of an epoxide to furnish the drimene core. Subsequent phenylselenonium ion induced diastereoselective cyclization of the drimene completed the essential carbon framework of the austalides to access (±)-17 S-dihydroaustalide K, (±)-austalide K, and (±)-13-deacetoxyaustalide I via sequential oxidations. Furthermore, (±)-13-deacetoxyaustalide I could serve as a common intermediate to be derivatized into other related natural products, (±)-austalide P and (±)-13-deoxyaustalide Q acid, by functionalizing the cyclic lactone moiety.
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