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The Revised Structure of Trichodermatide A
Author(s) -
Shigehisa Hiroki,
Kikuchi Harue,
Suzuki Tsuyoshi,
Hiroya Kou
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501281
Subject(s) - chemistry , epimer , stereochemistry , mitsunobu reaction , two dimensional nuclear magnetic resonance spectroscopy
A revised structure for trichodermatide A, which is a C10 epimer of the originally reported structure, is proposed. The revision is supported by the X‐ray structure of a synthetic intermediate synthesized according to our previous route for trichodermatide A. The revised stereochemistry was also supported by NOESY experiment. Finally, we synthesized Trauner's compound corresponding to the originally reported structure from our synthetic intermediate of trichodermatide A through a Mitsunobu reaction at C10.