TY - JOUR
T1 - Synthetic studies toward isoschizogamine
T2 - Construction of pentacyclic core structure
AU - Sugimoto, Kenji
AU - Fujiwara, Hiroaki
AU - Takada, Akihiro
AU - Kim, Dong Gil
AU - Ueda, Hirofumi
AU - Tokuyama, Hidetoshi
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Numbers JP16H01127 in Middle Molecular Strategy and JP16H00999 in Precisely Designed Catalysts with Customized Scaffolding, a Grant-in aid for Scientific Research (A) (26253001) and (C) (17K08204).
Publisher Copyright:
© 2018 The Japan Institute of Heterocyclic Chemistry
PY - 2018
Y1 - 2018
N2 - Development of a concise construction of the pentacyclic core skeleton of isoschizogamine was described. Tetracyclic A,B,D,F-rings structure was assembled by intramolecular aza-Diels–Alder reaction via an ortho-iminoquinone methide intermediate. The C-ring was formed by oxidation of the benzylic position with a combination of Cr(CO)6 and t-BuOOH, followed by the introduction of an aminoethyl side chain, C–H oxidation of the lactam ring with CrO3 and n-Bu4NI, and final cyclization to construct the cyclic aminal moiety.
AB - Development of a concise construction of the pentacyclic core skeleton of isoschizogamine was described. Tetracyclic A,B,D,F-rings structure was assembled by intramolecular aza-Diels–Alder reaction via an ortho-iminoquinone methide intermediate. The C-ring was formed by oxidation of the benzylic position with a combination of Cr(CO)6 and t-BuOOH, followed by the introduction of an aminoethyl side chain, C–H oxidation of the lactam ring with CrO3 and n-Bu4NI, and final cyclization to construct the cyclic aminal moiety.
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U2 - 10.3987/COM-18-S(T)85
DO - 10.3987/COM-18-S(T)85
M3 - Article
AN - SCOPUS:85069582749
SN - 0385-5414
VL - 97
SP - 1028
EP - 1049
JO - Heterocycles
JF - Heterocycles
IS - 2
ER -