去甲氧基去乙酰基白堅木鹼

去甲氧基去乙酰基白堅木鹼
	IUPAC名; (3aR,10bR)-3aβ-Ethyl-2,3,3a,4,5,5aα,6,11,12,13aβ-decahydro-1H-indolizino[8,1-cd]carbazole
識別
CAS號	2912-09-6（+） ; 32975-45-4（-） ; 7689-02-3（±）
PubChem	6857472
ChemSpider	5256809
SMILES	CC[C@]12CCCN3[C@H]1[C@]4(CC3)c5ccccc5N[C@@H]4CC2;
InChI	1/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3/t16-,17-,18-,19-/m1/s1;
InChIKey	YAAIPCQYJYPITK-NCXUSEDFBY
ChEBI	38486
性質
化學式	C19H26N2
摩爾質量	282.42 g·mol−1
外觀	淺黃色固體（+）; 白色固體（-）
熔點	118-120 °C（+）; 113-114 °C（-）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

去甲氧基去乙酰基白堅木鹼是從白堅木屬植物中提取出來的生物鹼，化學式為C₁₉H₂₆N₂。^[3]由於它的結構與很多重要的具有生物活性的分子相似^[4] ，它是全合成的熱門分子。^[5]^[6]^[7]^[8]

參考文獻

^ ^1.0 ^1.1 Ganesh Pandey, Shiva Kumar Burugu, and Pushpendra Singh. Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine. Org. Lett. 2016, 18, 7, 1558–1561. doi:10.1021/acs.orglett.6b00374.
^ ^2.0 ^2.1 Marius Mewald, Jonathan William Medley, Mohammad Movassaghi. Concise and Enantioselective Total Synthesis of (−)-Mehranine, (−)-Methylenebismehranine, and Related Aspidosperma Alkaloids. Angew Chem Int Ed. 2014. 53 (43). doi:10.1002/anie.201405609
^ Deutsch, Harold F.; Evenson, Merle A.; Drescher, Peter; Sparwasser, Christoph; Madsen, Paul O. Isolation and biological activity of aspidospermine and quebrachamine from an Aspidosperma tree source. Journal of Pharmaceutical and Biomedical Analysis. October 1994, 12 (10): 1283–1287. PMID 7841224. doi:10.1016/0731-7085(94)00066-2.
^ Anagnostaki, Elissavet E.; Zografos, Alexandros L. "Common synthetic scaffolds" in the synthesis of structurally diverse natural products. Chemical Society Reviews. 2012, 41 (17): 5613–25. PMID 22782134. doi:10.1039/c2cs35080g.
^ Marino, Joseph P.; Rubio, Maria B.; Cao, Ganfeng; de Dios, Alfonso. Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids. Journal of the American Chemical Society. November 2002, 124 (45): 13398–13399. PMID 12418888. doi:10.1021/ja026357f.
^ Jones, Spencer B.; Simmons, Bryon; Mastracchio, Anthony; MacMillan, David W. C. Collective synthesis of natural products by means of organocascade catalysis. Nature. 13 July 2011, 475 (7355): 183–188. PMC 3439143 . PMID 21753848. doi:10.1038/nature10232.
^ Ma, Haichen; Xie, Xingang; Jing, Peng; Zhang, Weiwei; She, Xuegong. Concise total synthesis of (±)-aspidospermidine. Org. Biomol. Chem. 2015, 13 (18): 5255–5259. PMID 25856579. doi:10.1039/C5OB00228A.
^ Callaghan, Owen; Lampard, Christopher; Kennedy, Alan R.; Murphy, John A. A novel total synthesis of (±)-aspidospermidine. Journal of the Chemical Society, Perkin Transactions 1. 1999, (8): 995–1002. doi:10.1039/A900335E.

[Pandey-1] 1.0 ^1.1 Ganesh Pandey, Shiva Kumar Burugu, and Pushpendra Singh. Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine. Org. Lett. 2016, 18, 7, 1558–1561. doi:10.1021/acs.orglett.6b00374.

[Marius-2] 2.0 ^2.1 Marius Mewald, Jonathan William Medley, Mohammad Movassaghi. Concise and Enantioselective Total Synthesis of (−)-Mehranine, (−)-Methylenebismehranine, and Related Aspidosperma Alkaloids. Angew Chem Int Ed. 2014. 53 (43). doi:10.1002/anie.201405609

[Isolation-3] Deutsch, Harold F.; Evenson, Merle A.; Drescher, Peter; Sparwasser, Christoph; Madsen, Paul O. Isolation and biological activity of aspidospermine and quebrachamine from an Aspidosperma tree source. Journal of Pharmaceutical and Biomedical Analysis. October 1994, 12 (10): 1283–1287. PMID 7841224. doi:10.1016/0731-7085(94)00066-2.

[4] Anagnostaki, Elissavet E.; Zografos, Alexandros L. "Common synthetic scaffolds" in the synthesis of structurally diverse natural products. Chemical Society Reviews. 2012, 41 (17): 5613–25. PMID 22782134. doi:10.1039/c2cs35080g.

[Marino-5] Marino, Joseph P.; Rubio, Maria B.; Cao, Ganfeng; de Dios, Alfonso. Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids. Journal of the American Chemical Society. November 2002, 124 (45): 13398–13399. PMID 12418888. doi:10.1021/ja026357f.

[Simmons-6] Jones, Spencer B.; Simmons, Bryon; Mastracchio, Anthony; MacMillan, David W. C. Collective synthesis of natural products by means of organocascade catalysis. Nature. 13 July 2011, 475 (7355): 183–188. PMC 3439143 . PMID 21753848. doi:10.1038/nature10232.

[Ma-7] Ma, Haichen; Xie, Xingang; Jing, Peng; Zhang, Weiwei; She, Xuegong. Concise total synthesis of (±)-aspidospermidine. Org. Biomol. Chem. 2015, 13 (18): 5255–5259. PMID 25856579. doi:10.1039/C5OB00228A.

[8] Callaghan, Owen; Lampard, Christopher; Kennedy, Alan R.; Murphy, John A. A novel total synthesis of (±)-aspidospermidine. Journal of the Chemical Society, Perkin Transactions 1. 1999, (8): 995–1002. doi:10.1039/A900335E.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]