@article {2107, title = {Synthetic studies toward halichlorine: Complex azaspirocycle formation with use of an NBS-promoted semipinacol reaction}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {11}, year = {2008}, note = {ISI Document Delivery No.: 307MRTimes Cited: 13Cited Reference Count: 90Hurley, Paul B. Dake, Gregory R.}, month = {Jun}, pages = {4131-4138}, type = {Article}, abstract = {The investigations of a synthetic route incorporating a NIBS-promoted semipinacol rearrangement to the 6-azaspiro[4.5]decane fragment within halichlorine (1) are presented. A convergent approach was pursued, utilizing two chiral, enantiomerically enriched building blocks, 2-trimethylstannyl piperidene 10 and substituted cyclobutanone 19. Noteworthy synthetic operations in this study include the following: (a) a highly diastereoselective NBS-promoted semipinacol reaction that established four stereogenic centers in ketone 25 and (b) the use of a N-p-toluenesulfonyl-2-iodo-2-piperidene as a precursor to a basic organometallic reagent, which was critical to the success of the coupling of fragments 10 and 19.}, keywords = {(+/-)-PINNAIC ACID, ASYMMETRIC-SYNTHESIS, BAEYER-VILLIGER OXIDATION, CARBOXYLIC-ACIDS, CRIEGEE REARRANGEMENT, ETHYLMAGNESIUM BROMIDE, ORGANIC-SYNTHESIS, PINNAIC ACID, RING-CLOSING METATHESIS, SPIROCYCLIC CORE}, isbn = {0022-3263}, url = {://000256323500018}, author = {Hurley, P. B. and Dake, G. R.} } @article {1373, title = {Recent approaches to the construction of 1-azaspiro[4.5]decanes and related 1-azaspirocycles}, journal = {Tetrahedron}, volume = {62}, number = {15}, year = {2006}, note = {ISI Document Delivery No.: 027TBTimes Cited: 25Cited Reference Count: 147}, month = {Apr}, pages = {3467-3492}, type = {Review}, keywords = {3 degrees carbon center, AROMATIC PI-NUCLEOPHILE, azaspirocyclic ring systems, DIELS-ALDER REACTION, DIPOLAR CYCLOADDITION ROUTES, FORMAL TOTAL-SYNTHESIS, HYPERVALENT, IMMUNOSUPPRESSANT FR901483, IODINE OXIDATION, MARINE ALKALOID LEPADIFORMINE, N-ACYLNITRENIUM IONS, OXIDATIVE RADICAL CYCLIZATION, POTENT, RING-CLOSING METATHESIS, spirocycles}, isbn = {0040-4020}, url = {://000236437400001}, author = {Dake, G. R.} }