N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• which is finally easily removed [11]. Among three-carbon chirons related to Garner’s aldehyde derivatives of N-(1-phenylethyl)aziridine-2-carboxylic acid 5–8 (Figure 2) play an important role in asymmetric synthesis as they function as a chiral synthon combined with a chiral auxiliary [(R)- or (S)-1

Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

• functionalities. Synthetic studies, also conducted by Nakamura and Uemura, established the absolute structure and configuration as (R)-(−)-complanine (Figure 1), showing it to be related to other natural products that possess the vicinal amino alcohol moiety. Using a chiral-synthon approach, (R)-(−)-complanine

(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study

• Kazuhiko Nakamura,
• Yu Tachikawa and
• Daisuke Uemura

Beilstein J. Org. Chem. 2009, 5, No. 12, doi:10.3762/bjoc.5.12

• inflammatory substance of Eurythoe complanata, was accomplished by a “chiral synthon” approach. The absolute configuration of this molecule was determined to be R. Keywords: chiral synthon; complanine; inflammatory substance; marine fireworm; total synthesis; Introduction Toxic marine annelids were first

• absolute structure of complanine was unambiguously determined by means of synthetic methodology by a “chiral synthon” approach. Related amino alcohols possessing olefins from marine natural resources have been identified [3][4], but synthetic studies of these compounds have not been reported. Results and