A New Antiherpetic Agent, AH-1763 IIa, Produced by Streptomyces cyaneus Strain No. 1763.

Enantioselective Total Synthesis and Structure Determination of the Antiherpetic Anthrapyran Antibiotic AH‐1763 IIa

“…The published 1 H NMR spectrum of the compound isolated by Uyeda et al1 and that of our synthetic (14 S ,16 R )‐AH‐1763 IIa ( 1 ) were identical in all respects, including chemical shifts and coupling constants. In addition, the 13 C NMR spectra deviated by at most 0.1 ppm.…”

“…This compound exhibits a remarkable inhibitory activity against Gram‐positive bacteria like Bacillus subtilis and Staphylococcus aureus 1. Moreover, it has a very strong antiherpetic activity (EC 50 =2.1 μg mL −1 against HSV‐1), which has so far not been observed for any other compound of the anthrapyran natural products 1. 4…”

“…The anthrapyran antibiotic AH‐1763 IIa ( 1 ) was isolated in 1997 by Uyeda et al1 from a culture broth of Streptomyces cyaneus . Compound 1 contains the 4 H ‐anthra[1,2‐ b ]pyran‐4,7,12‐trione nucleus 2 found in the pluramycin antibiotics (Figure 1) 2.…”

First enantiospecific Baker–Venkataraman-rearrangements aiming at the total synthesis of chiral anthrapyran antibiotics

“…[18][19][20][21] In addition, some representatives show interesting biological properties such as the new antitherpeutic agent, AH-1763 IIa, produced by the Streptomyces cyaneus strain 22 and recently prepared by synthesis, 23 or the novel neuronal cell protecting espicufolin 1, produced by a Streptomyces sp. 24 Another large group are rubiflavinones 2 [25][26][27] with an hexadiene side chain on C-2 or c-indomycinone 3 with a butanol side chain at C-2, 28 with a tertiary hydroxy group in the C-4 side chain.…”

Saliniquinones A - F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola

“…Partial determination of the absolute configuration of the two stereocentres at C-14 and C-16 was based on optical rotation and CD data, and comparison to a similar pluramycin-derived molecule, AH-1763 IIa. [6, 7] Compound 5 displayed similar Cotton effects to 6 , and opposite Cotton effects to 1 – 3 . Given C-14 is the only stereocentre in 6 , we suggest the configuration at C-14 be assigned as R .…”