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A Unified Strategy for the Total Synthesis of the Angucycline Antibiotics SF 2315A, Urdamycinone B, and the Shunt Metabolite 104–2
Author(s) -
Kim Kyungjin,
Boyd Vincent A.,
Sobti Aditya,
Sulikowski Gary A.
Publication year - 1997
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199700004
Subject(s) - chemistry , total synthesis , aromatization , stereochemistry , metabolite , cycloaddition , naphthoquinone , organic chemistry , catalysis , biochemistry
Total syntheses of the angucycline antibiotics SF 2315A ( 2 ), urdamycinone B ( 4 ), and the shunt metabolite 104–2 ( 5 ) are described, as well as an approach toward the synthesis of SF 2315B ( 3 ). All four syntheses feature a Diels–Alder cycloaddition between a bromojuglone derivative and an optically active diene ( 25a ), the latter derived from (–)‐quinic acid. Subsequent key transformations include (i) stereocontrolled introduction of ring fusion oxygen functionality featured in SF 2315A ( 2 ) and SF 2315 B ( 3 ), (ii) preparation of C‐glycosyl juglone 53 , and (iii) NMO mediated oxidative aromatization of 60.