New Corymine-Related Indole Alkaloids from Hunteria zeylanica in Thailand.

Subhadhirasakul, Sanan; Takayama, Hiromitsu; Miyabe, Yuhko; Aimi, Norio; Ponglux, Dhavadee; Sakai, Shin‐ichiro

doi:10.1248/cpb.42.2645

Cited by 24 publications

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“…[9] Twocoryminerelated indole alkaloids, N a -demethylcorymineand N a -demethyldeformylcorymine,w ere later isolated. [10] Corymine is structurally similar to vincorine (5) [7] but different from the strychnos alkaloid minfiensine (6). [11] While both 4 and 5 have the tetracyclic iminoethanocarbazole skeleton and as evenmembered azepanyl ring, 4 has an extra six-membered hemiacetal ring.…”

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confidence: 99%

Total Synthesis of (±)‐Corymine

et al. 2017

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The first total synthesis of the hexacyclic indole alkaloid (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3-bromooxindole to afford 3,3-disubstituted oxindole, b) the formation of a 12-membered cyclic enol ether by intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a highly stereoselective manner, and d) the SmI -mediated reductive C-O bond cleavage to remove the α-keto carboxyl group.

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confidence: 99%

Total Synthesis of (±)‐Corymine

et al. 2017

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“…Recent studies have shown that it exhibits glycine receptor antagonism . Two corymine‐related indole alkaloids, N a ‐demethylcorymine and N a ‐demethyldeformylcorymine, were later isolated . Corymine is structurally similar to vincorine ( 5 ) but different from the strychnos alkaloid minfiensine ( 6 ) .…”

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confidence: 99%

Total Synthesis of (±)‐Corymine

et al. 2017

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The first total synthesis of the hexacyclic indole alkaloid (±)‐corymine is described. Starting from the readily available N‐protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3‐bromooxindole to afford 3,3‐disubstituted oxindole, b) the formation of a 12‐membered cyclic enol ether by intramolecular O‐propargylation, immediately followed by propargyl Claisen rearrangement to provide the α‐allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a highly stereoselective manner, and d) the SmI2‐mediated reductive C−O bond cleavage to remove the α‐keto carboxyl group.

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“…deformylcorymine 16 and strictamine 17 , respectively. The transformations of 13 and 14 into these natural products were straightforward.…”

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confidence: 98%

Skeletal Rearrangements as Strategies for the Total Syntheses of Indole Alkaloids

Xie

2018

Synlett

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In this account, we summarize our recent efforts in the total syntheses of several indole alkaloids, including minfiensine, calophyline A, deformylcorymine, strictamine, and goniomitine. Our central theme is to utilize skeletal rearrangements as key strategies for generating complex structures.1 Introduction2 The Development of an Aza-Pinacol Rearrangement3 Applications of Aza-Pinacol Rearrangements in Total Syntheses4 Strategy Extension: The Total Synthesis of Goniomitine5 Conclusion

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New Corymine-Related Indole Alkaloids from Hunteria zeylanica in Thailand.

Cited by 24 publications

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Total Synthesis of (±)‐Corymine

Total Synthesis of (±)‐Corymine

Total Synthesis of (±)‐Corymine

Skeletal Rearrangements as Strategies for the Total Syntheses of Indole Alkaloids

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