- Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids
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Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.
- Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond
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p. 4732 - 4740
(2021/04/07)
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- A concise asymmetric total synthesis of (+)-fawcettimine
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A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/
- Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.
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- Efforts toward the synthesis of (+)-Lyconadin A
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Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod
- Karella, Satish,Raghavan, Sadagopan
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- Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization
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A protecting-group-free route for the total synthesis of (-)-lycopodine was demonstrated in only 8 steps from Wade's fawcettimine enone (12 steps from commercial availiable (R)-(+)-pulegone). The key core of this alkaloid was constructed through a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction, synchronously establishing the bridged B-ring and the C13 quaternary stereocenter. Importantly, the synthesis further features a new efficient approach for the preparation of other lycopodine-type alkaloids.
- Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong
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supporting information
p. 4328 - 4331
(2016/11/09)
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- Total synthesis of (+)-fawcettidine
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(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
- Kozak, Jennifer A.,Dake, Gregory R.
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scheme or table
p. 4221 - 4223
(2009/03/11)
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- Synthesis of termini-differentiated 6-carbon stereotetrads: An alkylative oxidation strategy for preparation of the C21-C26 segment of apoptolidin
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(graph presented) Two methods have been developed for the synthesis of epoxide 36. The first uses (+)-pulegone 25 as an enantiopure starting material and introduces the requisite intricacy of target 22 in 12 operations. The second method employs an enanti
- Chen, Yuzhong,Evarts Jr., Jerry B.,Torres, Eduardo,Fuchs, Philip L.
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p. 3571 - 3574
(2007/10/03)
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- Photochemical rearrangement of 2-phenylthio-1,3-cyclohexanediols to deoxysugars. Application to a stereospecific synthesis of (+)-cis-rose oxide
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The present paper reports the stereospecific synthesis of (+)-cis-rose oxide, the unnatural isomer of the fragrant oil isolated from Bulgarian roses and Bourbon geraniums. The synthesis serves to illustrate the potential of a new photochemical rearrangement of carbocycles to deoxysugars reported earlier.
- Gravel, Denis,Bordeleau, Josee
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p. 8035 - 8038
(2007/10/03)
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- Enantiospecific synthesis of rpr 107880 : A new non peptide substance P antagonist
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The synthesis of enantiomerically pure RPR 107880 is described. The synthetic strategy is based on the use of the readily available and inexpensive (R)-(+)-pulegone. Copyright
- Mutti, Stephane,Daubie, Christophe,Decalogne, Francois,Fournier, Robert,Rossi, Pierre
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p. 3125 - 3128
(2007/10/03)
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