TY - JOUR
T1 - Total Syntheses of Stoloniferol B and Penicitol A, and Structural Revision of Fusaraisochromanone
AU - Ohashi, Tatsuki
AU - Hosokawa, Seijiro
N1 - Funding Information:
The authors are grateful for financial support from the Kurata Memorial Hitachi Science and Technology Foundation, the Naito Foundation, the Sumitomo Foundation, and the Tokyo Biochemical Research Foundation.
PY - 2018/5/18
Y1 - 2018/5/18
N2 - The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.
AB - The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.
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U2 - 10.1021/acs.orglett.8b01048
DO - 10.1021/acs.orglett.8b01048
M3 - Article
C2 - 29715038
AN - SCOPUS:85047313015
SN - 1523-7060
VL - 20
SP - 3021
EP - 3024
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -