Abstract
Tetrahydroisoquinoline natural products are a kind of alkaloids containing various pharmacological activities. These structurally diverse alkaloids mainly consist of two subclasses, monotetrahydroisoquinolines (MTHI) and bistetrahydroisoquinolines (BTHI). Since its family member, Ecteinascidin-743 (INN: Trabectedin, trade name: Yondelis®), has been approved by European Union in 2007 and the FDA in 2015 for the treatment of advanced soft tissue tumors, the research on this kind of natural product is full of new vitality. Quinocarcin and lemonomycin share a common diazabicyclo[3.2.1]octane framework that belongs to the subclass of MTHI, and their excellent antitumor activity and challenging architecture have made them an ideal target for total synthesis. In this short review, the progress in the total synthesis of quinocarcin and lemonomycin is summarized.
Graphical Abstract
[http://dx.doi.org/10.7164/antibiotics.28.497] [PMID: 807549]
[http://dx.doi.org/10.1021/bi00606a014] [PMID: 567065]
[http://dx.doi.org/10.1016/0040-4039(92)80008-8]
[http://dx.doi.org/10.1016/S1074-5521(01)00082-5] [PMID: 11755394]
[http://dx.doi.org/10.1016/S0040-4020(00)00629-3]
[PMID: 9717828]
[http://dx.doi.org/10.1073/pnas.96.7.3496] [PMID: 10097064]
[http://dx.doi.org/10.1016/S1074-5521(02)00137-0] [PMID: 12031667]
[http://dx.doi.org/10.1016/S0040-4020(00)00972-8]
[http://dx.doi.org/10.1039/C4NP00051J] [PMID: 25273374]
[http://dx.doi.org/10.7164/antibiotics.44.479] [PMID: 2061191]
[http://dx.doi.org/10.1039/b804167a] [PMID: 19020681]
[PMID: 2434218]
[http://dx.doi.org/10.1038/nrd2487] [PMID: 19096380]
[http://dx.doi.org/10.1021/ja962480t]
[http://dx.doi.org/10.1021/acs.orglett.2c03357] [PMID: 36305771]
[http://dx.doi.org/10.1021/acs.orglett.0c01493] [PMID: 32437173]
[http://dx.doi.org/10.1021/acs.joc.9b01778] [PMID: 31523959]
[http://dx.doi.org/10.1021/ja408034x] [PMID: 24001124]
[http://dx.doi.org/10.1021/jo100788j] [PMID: 20557114]
[http://dx.doi.org/10.1021/ol034575n] [PMID: 12790537]
[http://dx.doi.org/10.1021/jo801159k] [PMID: 18687003]
[http://dx.doi.org/10.1021/np400538q] [PMID: 24070054]
[http://dx.doi.org/10.1021/ol990553i] [PMID: 10822537]
[http://dx.doi.org/10.1016/j.tetlet.2021.153498]
[http://dx.doi.org/10.1021/ol0062502] [PMID: 10956543]
[http://dx.doi.org/10.1039/C6OB01064D] [PMID: 27405490]
[http://dx.doi.org/10.1016/j.tet.2009.05.025]
[http://dx.doi.org/10.1016/j.tetlet.2007.03.113] [PMID: 19578531]
[http://dx.doi.org/10.1002/anie.200603179] [PMID: 17099922]
[http://dx.doi.org/10.1016/j.tet.2006.09.056]
[http://dx.doi.org/10.1002/anie.200503983] [PMID: 16496274]
[http://dx.doi.org/10.1021/ja026216d] [PMID: 12047173]
[http://dx.doi.org/10.1016/S0040-4039(00)00106-4]
[http://dx.doi.org/10.1021/ja00165a095]
[http://dx.doi.org/10.1021/ja0571794] [PMID: 16390134]
[http://dx.doi.org/10.1039/c1cc13992d] [PMID: 21863175]
[http://dx.doi.org/10.1002/ejoc.201601409]
[http://dx.doi.org/10.1126/science.aav3421] [PMID: 30573544]
[http://dx.doi.org/10.1021/acs.joc.6b00327] [PMID: 27019081]
[http://dx.doi.org/10.1002/1521-3773(20010417)40:8<1463::AID-ANIE1463>3.0.CO;2-8]
[http://dx.doi.org/10.1021/ja0174027] [PMID: 11902886]
[http://dx.doi.org/10.1021/cr010212u] [PMID: 11996547]
[http://dx.doi.org/10.6023/cjoc201504003]
[http://dx.doi.org/10.1002/cbdv.202300172] [PMID: 36939065]
[http://dx.doi.org/10.7164/antibiotics.36.468] [PMID: 6874563]
[http://dx.doi.org/10.1021/ja00223a052]
[http://dx.doi.org/10.1021/ja00033a089]
[http://dx.doi.org/10.1021/ja00076a036]
[http://dx.doi.org/10.1016/S0040-4020(01)80644-X]
[http://dx.doi.org/10.1351/pac199668030703]
[http://dx.doi.org/10.1021/ja056206n] [PMID: 16316220]
[http://dx.doi.org/10.1021/ja800662q] [PMID: 18454525]
[http://dx.doi.org/10.1021/acs.orglett.9b01511] [PMID: 31180224]
[http://dx.doi.org/10.1021/ja808112y] [PMID: 19035638]
[http://dx.doi.org/10.1002/ange.201205106]
[http://dx.doi.org/10.1002/chem.201300687] [PMID: 23681666]
[http://dx.doi.org/10.1016/j.tetlet.2012.09.030]
[http://dx.doi.org/10.1021/jo00126a031]
[PMID: 14289713]
[http://dx.doi.org/10.1021/ja039223q] [PMID: 14653730]
[http://dx.doi.org/10.1021/ja0535817] [PMID: 16144380]
[http://dx.doi.org/10.1055/s-2006-944225]
[http://dx.doi.org/10.1021/jo8027449] [PMID: 19196163]
[http://dx.doi.org/10.1055/s-0030-1259531]
[http://dx.doi.org/10.1055/s-2008-1078273]
[http://dx.doi.org/10.1002/chem.201202073] [PMID: 22848018]
[http://dx.doi.org/10.1016/j.tet.2013.05.009] [PMID: 25083002]
[http://dx.doi.org/10.1016/j.tet.2012.02.043]
[http://dx.doi.org/10.1021/ja01051a049]
[http://dx.doi.org/10.1039/D1QO00029B]
[http://dx.doi.org/10.1016/j.ejmech.2013.01.033] [PMID: 23434640]
[http://dx.doi.org/10.1016/j.tetlet.2018.07.027]