Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E.

DOI: 10.1248/cpb.43.777

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 777 - 782 (1995)

Update date:2022-08-05

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Authors:

Saito Saito

Harada Harada

Nishida Nishida

Inouye Inouye

Kubo Kubo

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Article abstract of DOI:10.1248/cpb.43.777

Treatment of (-)-saframycin A (1a) with selenium oxide in acetic acid afforded (-)-saframycin G (1g), and a catalytic reduction and regioselective oxidation sequence afforded the saframycin Mx type compound (3). We applied this methodology to the transformation of (±)-5-hydroxysaframycin B (11) to the hydroquinone (1e). Acetylation of 1e with acetic anhydride in pyridine gave the triacetate (13), which is identical with the triacetyl derivative of natural saframycin E.

Full text of DOI:10.1248/cpb.43.777

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