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Synthesis of (+)-8-deoxyvernolepin

AuthorsHernández, Rosendo ; Velázquez, Silvia M. ; Suárez, Ernesto
Issue DateOct-1994
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 59(21): 6395-6403 (1994)
AbstractA short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-α-santonin (8), by functionalization of the angular methyl from a 2β- or 6β-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and l,4-fragmentation of the γ-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described. The most important structural features of this compound and other vernolepin congeners, the δ-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.
Description9 pages, 1 figure, 6 schemes.-- Supplementary Material Available: 1H NMR and 13C NMR spectra of compounds 7, 10, 11, 16-18, 21-23, 25, 26, 28-30, and 32-37, and 1H NMR spectrum of compounds 38 (41 pages).
Publisher version (URL)http://dx.doi.org/10.1021/jo00100a049
Appears in Collections:(IPNA) Artículos
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