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Synfacts 2018; 14(02): 0111
DOI: 10.1055/s-0037-1609193
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Himalensine A

Contributor(s):
Erick M. Carreira
,
Matthieu J. R. Richter
Shi H. Michaelides IN. Darses B. Jakubec P. Nguyen QN. N. Paton RS. * Dixon DJ. * University of Oxford, UK
Total Synthesis of (–)-Himalensine A.

J. Am. Chem. Soc. 2017;
139: 17755-17758
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Further Information

Publication History

Publication Date:
18 January 2018 (online)

 
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Key words

(–)-himalensine A - daphniphyllum alkaloid - amidofuran - Diels–Alder reaction - Negishi coupling - Stetter cyclization

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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