Helvetica Chimica Acta p. 1278 - 1290 (1995)
Update date:2022-08-04
Topics:
Su
Tamm
A new general concept for the total synthesis of pseurotin A (1), a secondary metabolite of Pseudeurotium ovalis STOLK, which possesses a highly substituted 1-oxa-7-azaspiro[4.4]nonane skeleton, is presented. A key intermediate of the planned reaction sequence is the functionalized γ-lactone 8. The corresponding protected compound 52 was prepared using (S)-O,O-isopropylideneglyceraldehyde (13) and the bromoacetal 14 as starting material. γ-Lactone 52 was obtained in enantiomerically pure state in ten steps. It possesses the desired configuration.
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Doi:10.1021/jm00022a015
(1995)Doi:10.1021/ja9531586
(1996)Doi:10.1016/0008-6215(95)00147-L
(1995)Doi:10.1021/acs.orglett.6b02689
(2016)Doi:10.1002/anie.201404352
(2014)Doi:10.1016/0040-4039(95)01674-7
(1995)
