Chemical and Pharmaceutical Bulletin p. 32 - 35 (1992)
Update date:2022-08-11
Topics:
Fujioka
Yamamoto
Annoura
Maeda
Kita
A new chiral AB-synthon, (5R,6R)-6-ethyl-5,6-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone (4), for the synthesis of optically active rhodomycinones was prepared stereoselectively from a (-)-α-hydroxy ketone (6). The coupling reactions of 4 with homophthalic anhydride derivatives (9, 12) proceeded in a regioselective manner to give the tetracyclic compounds 10 and 13, respectively. Compound 10 was converted to (-)-γ-rhodomycinone (3) in a two-step sequence. The optical purity (100% ee) of 3 was unambiguously determined by high performance liquid chromatography analysis using a chiral column.
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Doi:10.1080/00304940209355745
(1891)Doi:10.1021/acs.orglett.5b02568
(2015)Doi:10.5560/ZNB.2013-3033
(2013)Doi:10.1039/jr9520000993
(1952)Doi:10.1039/c4cc01312c
(2014)Doi:10.1039/b502866c
(2005)