Tetrahedron p. 14359 - 14376 (1998)
Update date:2022-09-26
Topics:
Baxter, John
Mata, Ernesto G.
Thomas, Eric J.
The organolithium reagent generated from the vinyl iodide 8 reacts with aldehyde 13 to give a mixture of the anti- and syn-silyloxy alcohols 14 and 15 together with the regioisomeric syn-silyloxy alcohol 16, ratio 14 : 15: 16 = 4 : 1 : 1. The major anti-alcohol 14 was taken through to the methoxyacetal 27 so confirming this strategy for the stereoselective synthesis of the C(17)-C(23) fragment of bryostatins. The diol 30, which has configurations at each of its three chiral centres corresponding to the C(23)-C(27) fragment of bryostatins, was prepared in two steps from the aldehyde 28 and converted into the vinylstannane 45.
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Doi:10.1021/jo980618f
(1998)Doi:10.1016/S0040-4039(98)01998-4
(1998)Doi:10.1002/anie.201701481
(2017)Doi:10.1016/s0020-1693(98)00296-5
(1999)Doi:10.1007/BF01169901
()Doi:10.1007/BF02251694
(1998)