88088-55-5Relevant articles and documents
Synthesis of the oudemansins, naturally occurring β-methoxyacrylates from basidomycetes
Wittman,Kallmerten
, p. 4303 - 4307 (2007/10/02)
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-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM; AN EMERGING TOOL FOR CONTROL OF ACYCLIC STEREOCHEMISTRY
Mikami, Koichi,Azuma, Ken-Ichi,Nakai, Takeshi
, p. 2303 - 2308 (2007/10/02)
The -Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds.Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (+/-)-oudemansin.Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond.