A concise enantioselective route to (–)-kainic acid from (S)-2-(benzyloxymethyl)oxirane

Abstract

A concise enantioselective route t o (-)-kainic acid (1) from (S)-2-(benzyloxymethyl)oxirane (2) has been established by ena n tio-and diastereo-selective i nt ramolecu la r 1,3-d i pola r cycl ization.

A concise synthesis of (+)-muscarine

“…Synthesis of muscarine has been accomplished a number of times from different precursors (2)(3)(4)(5)(6). Recently, a chemoenzymatic synthesis of muscarine and its stereoisomers has been reported (7).…”

Using the COSYMA System for the Discovery of Synthesis Strategies by Analogy

“…Figure 2 shows some of the strategies ''learned'' by COSYMA, starting from a synthesis of kainic acid proposed by Takano. [11] BACOCO (COSYMA Knowledge Base)…”

An efficient strategy for the construction of X-azatricyclo[m.n.0.0a,b]alkanes by intramolecular [3+2]cyclo­addition of nonstabilised cyclic azomethine ylides

“…The interest of constructing skeletons of type 7 was further enlightened by the recent disclosure of Smith et al 27,28 that the rigid cocaine analogues (8)(9)(10) having azatricyclo ring systems show high binding affinity to the site of the monoamine transporters. The enhanced selectivity of these rigid tropane analogues for the monoamine transporter inhibitors is understood to be influenced by the fixed orientation of the nitrogen lone pair due to the tethered carbon bridge of the tropane moiety.…”

“…The 1,3-dipolar cycloaddition of azomethine ylides with olefinic dipolarophile is identified as one of the most attractive strategy for the construction of isolated as well as fused pyrrolidine ring systems. 2, 3 Taking the advantage of the regio-and stereoselectivity of such cycloadditions, compounds possessing complex molecular framework such as eserethole, 4 erythramine, 5 α-lycorane, 6 allokainic acid, 7 acromelic acid, 8 (-)-kainic acid, 9 sceletium alkaloid A4, 10 menzamine alkaloids, 11 martinelline alkaloids 12 and various other bicyclic 13- …”