Premium
Biomimetic Synthesis of the Racemic Angucyclinones of the Aquayamycin and WP 3688‐2 Types
Author(s) -
Krohn Karsten,
Frese Peter,
Flörke Ulrich
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20001103)6:21<3887::aid-chem3887>3.0.co;2-3
Subject(s) - chemistry , stereochemistry , bicyclic molecule
The first synthesis of the racemic 8‐deoxy WP 3688‐2 angucycline antibiotic ( 3 ), with characteristic cis‐ hydroxy groups at C‐4 a and C‐12 b, is reported. Key steps involve the coupling, mediated by samarium diiodide, of the bicyclic trione 37 to the tricyclic cis‐ diol 39 . Biomimetic aldol cyclization of the corresponding dione 41 gave a mixture of the tetracyclic cis‐ and trans‐ 3,4 a‐diols 42 and 43 , which were oxidized by cerium ammonium nitrate to the quinones 45 and 3 . The synthetic compounds 45 and 3 corresponded in configuration to the angucycline antibiotics aquayamicin ( 1 ) and WP 3688‐2 ( 2 ), respectively.