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Synfacts 2018; 14(02): 0111
DOI: 10.1055/s-0037-1609193
DOI: 10.1055/s-0037-1609193
Synthesis of Natural Products and Potential Drugs
Synthesis of (–)-Himalensine A
Further Information
Publication History
Publication Date:
18 January 2018 (online)
Key words
(–)-himalensine A - daphniphyllum alkaloid - amidofuran - Diels–Alder reaction - Negishi coupling - Stetter cyclization![](https://www.thieme-connect.de/media/synfacts/201802/i_c079_s1_10-1055_s-0037-1609193.gif)
Significance
(–)-Himalensine A is a highly congested alkaloid featuring a trinorcalyciphylline A skeleton. Dixon, Paton, and co-workers report its first enantioselective synthesis in 23 steps involving an intramolecular amidofuran Diels–Alder reaction (see also Synfacts 2018, 14, 203).
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Comment
The enantioselective, intramolecular Diels–Alder reaction of B afforded tetracycle D. A Stetter cyclization of L using NHC catalyst M forged the final ring of the carbon framework. Subsequent amide reduction completed the total synthesis.
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![](https://www.thieme-connect.de/media/synfacts/201802/i_c079_s1_10-1055_s-0037-1609193.gif)