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Open AccessArticle

Synthesis of Natural (−)-Antrocin and Its Enantiomer via Stereoselective Aldol Reaction

1
Department of Chemistry, Pondicherry University, Puducherry 605014, India
2
Department of Chemistry, National Dong Hwa University, Shoufeng Township, Hualien County 974, Taiwan
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(4), 831; https://doi.org/10.3390/molecules25040831
Received: 15 January 2020 / Revised: 7 February 2020 / Accepted: 13 February 2020 / Published: 14 February 2020
(This article belongs to the Special Issue Chemistry of Natural Organic Compounds)
The total synthesis of (−)-antrocin and its enantiomer are presented. Antrocin (−)-1 is an important natural product which acts as an antiproliferative agent in a metastatic breast cancer cell line (IC50: 0.6 μM). The key features of this synthesis are: (a) selective anti-addition of trimethylsilyl cyanide (TMSCN) to α,β-unsaturated ketone; (b) resolution of (±)-7 using chiral auxiliary L-dimethyl tartrate through formation of cyclic ketal diastereomers followed by simple column chromatography separation and acid hydrolysis; (c) substrate-controlled stereoselective aldol condensation of (+)-12 with monomeric formaldehyde and pyridinium chlorochromate (PCC) oxidation for synthesis of essential lactone core in (−)-14; and (d) non-basic Lombardo olefination of the carbonyl at the final step to yield (−)-antrocin. In addition, (+)-9 cyclic ketal diastereomer was converted to (+)-antrocin with similar reaction sequences. View Full-Text
Keywords: (−)-antrocin; diastereoselective aldol reaction; chiral resolution; natural product synthesis; non-basic Lombardo olefination (−)-antrocin; diastereoselective aldol reaction; chiral resolution; natural product synthesis; non-basic Lombardo olefination
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MDPI and ACS Style

Angamuthu, V.; Tai, D.-F. Synthesis of Natural (−)-Antrocin and Its Enantiomer via Stereoselective Aldol Reaction. Molecules 2020, 25, 831.

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