Tetrahedron p. 12843 - 12852 (1994)
Update date:2022-08-05
Topics: Total synthesis Natural product Confirmation (+)-Spatol Absolute stereostructure
Tanaka, Masahide
Tomioka, Kiyoshi
Koga, Kenji
Total synthesis of optically pure spatol (+)-1 was achieved by employing asymmetric (2+2) photocycloaddition of the optically pure 12 with cyclopentenone ethylene ketal.The two major photocycloadducts 14, 15 were separately converted into the cis,anti,cis-tricyclo<5.3.0.02,6>decane 9 and then to the sulfonium 11.Coupling of 11 through ylide with optically active epoxyaldehyde 24 provided optically pure 1 with definite absolute configuration.
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Doi:10.1134/S0965544114030074
(2014)Doi:10.1002/ardp.201300471
(2014)Doi:10.1002/chem.201400112
(2014)Doi:10.1021/ja00989a031
(1967)Doi:10.1021/acs.orglett.1c00313
(2021)Doi:10.1016/S0040-4039(00)73430-7
(1994)