Journal of Organic Chemistry p. 4823 - 4832 (1993)
Update date:2022-08-05
Topics:
McIntosh, Matthias C.
Weinreb, Steven M.
A convergent synthesis of a protected version of (+)-lycoricidine has been accomplished in 13 steps from L-arabinose.Preparation of the aminocyclitol moiety 50 employed a novel vinylsilane-terminated N-sulfonyliminium ion cyclization of vinylsilane aldehyde 42.Closure of the B-ring using an intramolecular Heck reaction afforded lycoricidine derivative 58.An unexpected cyclization of vinylsilane aldehyde 42 allowed for the stereodivergent preparation of semiprotected conduritols 43 and 45.
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