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Total Synthesis of Natural (+)‐SF 2315A and Determination of the Absolute Configuration
Author(s) -
Kim Kyungjin,
Sulikowski Gary A.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199523961
Subject(s) - total synthesis , ring (chemistry) , absolute configuration , chemistry , stereochemistry , diene , transformation (genetics) , organic chemistry , biochemistry , natural rubber , gene
An angucycline antibiotic with a nonaromatic B ring , (+)‐SF 2315A ( 3 ), was synthesized enantioselectively for the first time. A key transformation in the 23‐step reaction sequence, which starts from (−)‐quinic acid, is the stereocontrolled Diels‐Alder reaction between diene 1 and bromojuglone 2 . TIPS = triisopropylsilyl.
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