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
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).
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.
