Phenyliodosyl bis trifluoroacetate

RNH2 (R=alkyl, but not aryl) are phenyliodosyl bis(trifluoroacetate), Phl(0-C0CF3)2 and hydroxy(tosyloxy)iodobenzene, PhI(OH)OTs. A mixture of NBS, Hg(OAc)2, and R OH is one of several reagent mixtures that convert an amide (RCONH2) to the carbamate (RNHCOOR ) (R=primary, secondary, or tertiary... 

The synthesis of the spirocyclic core [70-77] is obviously the most difficult task, the biomimetic approach being the most frequent way of preparing it. The strategy is based on the hipervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative followed by a cis-bisepoxidation. The shortest way [75] involved the introduction of the side chain as an amide of tyrosine ethyl ester. Aranorosin was obtained after DIBAL reduction to the aldehyde, oxidation to the dienone with phenyliodosyl bis(trifluoroacetate) (PIFA) and final epoxidation (Scheme 24). 

Phenylbis trifluoroacetato-0)iodine, 9CI. lodobenzene 1,1-ditrifluoroacetate. Phenyliodosoditrifluoroacetate. lodobenzene bis(trifluoroacetate). Phenyliodosyl bis trifluoroacetate)... 

Some specific reagents of importance to this review are shown in Table I and are identified with names commonly used in the literature selected acronyms are also given. The reader is alerted, however, that while some acronyms (HTIB, IBX, DMP) appear to have gained general acceptance, others depend on the nomenclature preferences of individual authors. For example, PhI(OAc)2 is variously designated in the literature as DAIB, DIB, BAIB, IBD, PID, PIA, and PIDA. Acronyms for PhI(OCOCF3)2 include BTIB, BTI, IBTA, and most commonly PIFA [i.e., for phenyliodosyl- or phenyiodine(III) bis(trifluoroacetate)]. 

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