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Synlett 2000; 2000(11): 1667-1669
DOI: 10.1055/s-2000-7950
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Total Synthesis of Lipogrammistin-A: Efficient Macrocyclization with 2-Nitrobenzenesulfonamide

Akiko Fujiwara* , Toshiyuki Kan, Tohru Fukuyama
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, The Japan Science and Technology Corporation (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax +81-3-58 02-86-94; E-mail: fukuyama@mol.f.u-tokyo.ac.jp
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Publication Date:
31 December 2000 (online)

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Total synthesis of lipogrammistin-A (1) was accomplished using a 2-nitrobenzenesulfonyl (Ns) group for both protection and activation of amines. The β-amino ester derivative 16 was synthesized from carboxylic acid 12 in six steps by way of reduction to the aldehyde and the subsequent Wittig olefination. N-Alkylation of the Ns group under Mitsunobu conditions followed by amide formation provided 20. Intramolecular alkylation of the Ns group in 20 gave the 18-membered ring 21 as the exclusive product. After removal of the Ns group, selective acylation of the two of the three amino groups with (S)-2-methylbutyric acid furnished the desired compound 1.

lipogrammistin-A - 2-nitrobenzenesulfonamide - nosyl group (Ns) - macrocyclization - alkylation - Mitsunobu reaction