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Rearrangement of spiroacetals of the 1,6-Dioxaspiro[4.5]decan-10-yl methanesulfonate type. Synthesis of cis-fused 1,6-dioxadecalins

AuthorsBetancor, Carmen; Dorta, Rosa L. ; Freire, Raimundo ; Prangé, Thierry; Suárez, Ernesto
Issue Date17-Nov-2000
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 65(25): 8822-8825 (2000)
AbstractCompounds isolated from marine sources such as maitotoxin (MXT) and halichondrins consist mainly of fused polycyclic ethers, a remarkable structural feature being the presence of two sets of cis-fused ether rings: rings A/B and F/G in the halichondrins and rings L/M and N/O in maitotoxin.
The important biological activity of such compounds and their complex structures make them interesting targets in natural products chemistry.
We have recently described a new method for the synthesis of steroidal cis- and trans-fused ditetrahydropyrans by reduction with DIBALH of steroidal methanosulfonates.
Description4 pages, 3 schemes.-- Printed version published Dec 15, 2000.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo005593a
Erratum to this paper published in: J. Org. Chem. 69(26): 9323 (2004), http://dx.doi.org/10.1021/jo040014d
Publisher version (URL)http://dx.doi.org/10.1021/jo005593a
Appears in Collections:(IPNA) Artículos
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