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The first total synthesis of roquefortine D

✍ Scribed by Wei-Chuan Chen; Madeleine M. Joullié

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 189 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01957-1

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✦ Synopsis

The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o-nitrobenzyl group was utilized for histidine side chain protection, and the cyclization to the diketopiperazine was carried out under mild conditions.

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