- Bioinspired total synthesis of montanine-type amaryllidaceae alkaloids
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Finding a common path: A synthetic strategy inspired by the proposed biogenesis of the montanine-type alkaloids enabled the concise asymmetric synthesis of these compounds in a divergent fashion on the basis of an unprecedented tandem oxidative dearomatization/intramolecular aza-Michael addition as the key step. This bioinspired approach revealed a chemical connection between the cherylline- and montanine-type alkaloids (see scheme). Copyright
- Bao, Xu,Cao, Ye-Xing,Chu, Wen-Dao,Qu, Hu,Du, Ji-Yuan,Zhao, Xian-He,Ma, Xiao-Yan,Wang, Cheng-Tao,Fan, Chun-An
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p. 14167 - 14172
(2014/01/06)
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- An expedient route to montanine-type amaryllidaceae alkaloids: Total syntheses of (-)-brunsvigine and (-)-manthine
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(Chemical Equation Presented) The first total syntheses of (-)-brunsvigine (1) and (-)-manthine (2) were accomplished in 10 and 18 steps, respectively. (-)-Quinic acid was converted to enone 12 in live steps. Iodination of enone 12 followed by stereoselec
- Hong, An-Wei,Cheng, Tsung-Hui,Raghukumar, Vellingiri,Sha, Chin-Kang
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p. 7580 - 7585
(2008/12/22)
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- Synthesis of aza bicyclic enones via anionic cyclization: Application to the total synthesis of (-)-brunsvigine
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(Matrix presented) A general approach to the synthesis of aza bicyclic enones was developed via a simple two-step annulation involving a Mitsunobu protocol and anionic cyclization. According to this strategy the total synthesis of (-)-brunsvigine was acco
- Sha, Chin-Kang,Hong, An-Wei,Huang, Chien-Ming
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p. 2177 - 2179
(2007/10/03)
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- A FIRST TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-COCCININE, (+/-)-MONTANINE, AND (+/-)-PANCRACINE
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Montanine-type Amaryllidaceae alkaloids, (+/-)-coccinine (1), (+/-)-montanine (2), and (+/-)-pancracine (3) were synthesized starting from (+/-)-1,2-cis-2-(3,4-methylenedioxybenzoyl)cyclohex-4-enecarboxylic acid (6) via (+/-)-2,3-cis-3-benzyloxy-2-hydroxy
- Ishizaki, Miyuki,Hoshino, Osamu,Iitaka, Yoichi
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p. 7079 - 7082
(2007/10/02)
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- First Total Synthesis of Amaryllidaceae Alkaloids of the 5,11-Methanomorphanthridine Type. An Efficient Total Synthesis of (+/-)-Pancracine
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A tandem aza-Cope rearrangement-Mannich cyclization (9 -> 3) is the central step in a concise total synthesis of (+/-)-pancracine.
- Overman, Larry E.,Shim, Jaechul
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p. 5005 - 5007
(2007/10/02)
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