Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.
Total synthesis of the Lycopodium alkaloid lyconadin A was achieved in 18 steps starting from a readily available vinylogous ester and bromopicoline. The key step in the total synthesis is a proximity-driven oxidative C-N bond-forming reaction that yields the lyconadin pentacycle from a tetracyclic precursor. The key tetracycle, which has been prepared for the first time, is a versatile intermediate that may be utilized for the total synthesis of a variety of Lycopodium alkaloids. Critical to the success of this plan was the efficient preparation of a pyridine-annulated cycloheptadiene tricycle that promises to be a general strategy to access a variety of seven-membered ring containing natural products.
Bisai
Alakesh
A
Department of Chemistry, University of California, Berkeley, California 94720, USA.
West
Scott P
SP
Sarpong
Richmond
R
D000470:Alkaloids / Q000138:chemical synthesis*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
D000470:Alkaloids; D011083:Polycyclic Compounds; C435307:lyconadin A