✦ LIBER ✦
New routes to the syntheses of cis-α-(carboxycyclopropyl)glycines from L-glutamic acid. conformationally restricted analogues of the excitatory neurotransmitter L-glutamic acid
✍ Scribed by Keiko Shimamoto; Yasufumi Ohfune
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 140 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
3804
with NaH provided the pyrrolidone in which the Boc group was cleaved under the reaction conditions. This group was reintroduced with Boc20 to give 7 [87% from 3, oil, [a]D -62.2" (c 1.23, CHCl3)]. Unsaturated 8 was prepared using the reported method. 7 Cyclopropanation of 4 and 8 was carried out with CH2N2 in the presence of catalytic Pd(OAc)2 From Uactone 4, the (35,4R)-isomer 5 was produced as the major product (6/i, 46%). This was converted into CCG-IV using reported procedure.2a Pyrrolidone 8 gave