The first total synthesis of roquefortine D

DOI: 10.1016/S0040-4039(98)01957-1

Source and publish data:

Tetrahedron Letters p. 8401 - 8404 (1998)

Update date:2022-08-03

Topics: Solid-phase synthesis Microwave-assisted synthesis Yield NMR spectroscopy Mass spectrometry HPLC Enantiomeric excess (ee) Total synthesis Cyclization Protecting group X-ray crystallography Retrosynthetic analysis Chiral Resolution Coupling Reaction Oxidation/Reduction Natural product Indole alkaloid tryptophan Prenylation

Authors:

Chen, Wei-Chuan

Joullie, Madeleine M.

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Article abstract of DOI:10.1016/S0040-4039(98)01957-1

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.

Full text of DOI:10.1016/S0040-4039(98)01957-1

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