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Synthesis of atromentin and its O-alkylated natural products.

Bioscience, biotechnology, and biochemistry (2010-11-13)
Yue Qi Ye, Hiroyuki Koshino, Naoki Abe, Takemichi Nakamura, Daisuke Hashizume, Shunya Takahashi
ABSTRACT

The structure of a long-known natural pigment, atromentin, was established by a total synthesis based on double Suzuki-Miyaura coupling and by a single-crystal X-ray analysis of the synthetic sample thereby obtained. A similar strategy including ceric ammonium nitrate (CAN) oxidation was applied to prepare 2-O-methoxyatromentin and thelephantin I.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ammonium cerium(IV) nitrate, JIS special grade, ≥95.0%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥99.99% trace metals basis
Sigma-Aldrich
Ammonium cerium(IV) nitrate, puriss. p.a., ACS reagent, ≥98.5% (RT)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥98% (titration)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ACS reagent, ≥98.5%