Tetrahedron Letters p. 9 - 12 (1999)
Update date:2022-08-03
Topics:
Burke, Steven D.
Letourneau, Jeffrey J.
Matulenko, Mark A.
The total synthesis of (+)-breynolide (2) is described. The primary focus is the synthesis of the advanced aldehyde intermediate 12, which comprises the cis-fused perhydrobenzothiophene ring system. Three stereoselectiye cyclohexene epoxidation/epoxide opening sequences and a glycolate ester Claisen rearrangement, by which all of the necessary oxygen functionality in 12 is introduced before installation of the thioether, are employed.
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Doi:10.1002/(sici)1521-3765(19990104)5:1<274::aid-chem274>3.0.co;2-p
(1999)Doi:10.1016/S0022-328X(96)06725-3
(1997)Doi:10.1080/15257779908043070
(1999)Doi:10.1080/15257779908043064
(1999)Doi:10.1515/znb-1999-0108
(1999)Doi:10.1039/a808266i
(1999)
