14912-31-3Relevant academic research and scientific papers
Divergent and efficient syntheses of the Lycopodium alkaloids (-)-Lycojaponicumin C, (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-fawcettidine
Hou, Si-Hua,Tu, Yong-Qiang,Liu, Lin,Zhang, Fu-Min,Wang, Shao-Hua,Zhang, Xiao-Ming
, p. 11373 - 11376 (2013)
Four from one: The four title alkaloids (structures shown in blue box) have been synthesized by using a common versatile intermediate with a 6/5/5 tricyclic skeleton. This tricyclic intermediate could be easily assembled by using an intramolecular carbene addition/cyclization and a Dieckmann condensation/Tsuji-Trost allylation as key steps. Copyright
Enantioselective divergent total syntheses of fawcettimine-type Lycopodium alkaloids
Zeng, Chen,Zhao, Jingyun,Zhao, Gang
, p. 64 - 69 (2014)
Enantioselective divergent total syntheses of (+)-fawcettimine, (+)-fawcettidine, (+)-lycoflexine, (+)-lycoposerramine Q, (-)-Huperzine Q and (+)-N-oxyhuperzine Q have been described from a common precursor. The syntheses feature a vinylogous Rubottom oxidation and several biomimetic transformations.
Concise unified access to (-)-8-deoxy-13-dehydroserratinine, (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine using a direct intramolecular reductive coupling
Huang, Bing-Bing,Wang, Shaozhong,Yang, Xiao-Liang,Yao, Zhu-Jun,Zhong, Lin-Rui
, p. 3578 - 3583 (2021)
A short, scalable, and collective total synthesis of four fawcettimine-type Lycopodium alkaloids in eight or nine steps is disclosed. A dense multi-small-ring spiro-α-aminocyclopentanone successfully served as the key intermediate, which was directly acce
Unified total syntheses of fawcettimine class alkaloids: Fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B
Pan, Guojun,Williams, Robert M.
, p. 4801 - 4811 (2012)
The total syntheses of the lycopodium alkaloids fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy that relies on a Diels-Alder reaction to construct the cis-fused 6,5-carbocycles with one all-carbon quaternary center. Access to the enantioselective syntheses of both antipodes of those alkaloids can be achieved by kinetic resolution of the earliest intermediate via a Sharpless asymmetric dihydroxylation (Sharpless AD). Compared to existing approaches to these alkaloids, our synthetic route possesses superior stereocontrol over the C-4 and C-15 stereogenic centers as well as allowing for more functional variation on the 6-membered ring.
Divergent total syntheses of (-)-lycopladine D, (+)-fawcettidine, and (+)-lycoposerramine Q
Zeng, Chen,Zheng, Changwu,Zhao, Jingyun,Zhao, Gang
, p. 5846 - 5849 (2013)
Enantioselective total syntheses of (+)-fawcettidine and (+)-lycoposerramine Q as well as the first total synthesis of (-)-lycopladine D from a common intermediate have been accomplished by a divergent path. The common intermediate was derived from a Hajos-Parrish-like diketone by a stereoselective Birch reduction and a Suzuki coupling. The synthesis of (-)-lycopladine D featured an allylic oxidation and a biomimetic aminoketalization while the route to (+)-fawcettidine and (+)-lycoposerramine Q highlighted an oxidative rearrangement.
Collective synthesis of lycopodium alkaloids and tautomer locking strategy for the total synthesis of (-)-lycojapodine A
Li, Houhua,Wang, Xiaoming,Hong, Benke,Lei, Xiaoguang
, p. 800 - 821 (2013/04/23)
The collective total synthesis of Lycopodium alkaloids (+)-fawcettimine (1), (+)-fawcettidine (2), (+)-alopecuridine (4), (-)-lycojapodine A (6), and (-)-8-deoxyserratinine (7) has been accomplished from a common precursor (15) based on a highly concise route inspired by the proposed biosynthesis of the fawcettimine- and serratinine-type alkaloids. An intramolecular C-alkylation enabled efficient installation of the challenging spiro quaternary carbon center and the aza-cyclononane ring. The preparation of the tricyclic skeleton as well as the establishment of the correct relative stereochemistry of the oxa-quaternary center were achieved by hydroxyl-directed SmI2- mediated pinacol couplings. An unprecedented tandem transannular N-alkylation and removal of a Boc group was discovered to realize a biosynthesis-inspired process to furnish the desired tetracyclic skeleton. Of particular note is the unique and crucial tautomer locking strategy employed to complete the enantioselective total synthesis of (-)-lycojapodine A (6). The central step in this synthesis is the late-stage hypervalent iodine oxidant (IBX or Dess-Martin periodinane)/TFA-mediated tandem process, which constructed the previously unknown carbinolamine lactone motif and enabled a biomimetic transformation to generate (-)-lycojapodine A (6) in a single operation.
Total syntheses of lycopodium alkaloids (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine
Li, Houhua,Wang, Xiaoming,Lei, Xiaoguang
supporting information; experimental part, p. 491 - 495 (2012/02/16)
A shared story: Three fawcettimine- and serratinine-type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis-inspired
Total synthesis of (+)-fawcettidine
Kozak, Jennifer A.,Dake, Gregory R.
supporting information; experimental part, p. 4221 - 4223 (2009/03/11)
(Chemical Equation Presented) Alkaloids alchemy: A synthesis of the Lycopodium alkaloid (+)-fawcettidine (see structure) has been developed which requires 16 steps from (R)-(+)-pulegone as the chiral starting material. Key steps include a platinum(II)-cat
