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Synthesis of trans-syn-trans fused bis-pyrans via endo-selective cyclizations of cyclic sulfates

โœ Scribed by Frank E. McDonald; Prahlad Vadapally

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
250 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Acid-catalyzed cyclization of hydroxy-cyclic sulfates occurs with endo-regioselectivity affording bispyran products from substrates in which the nucleophilic hydroxyl and electrophilic cyclic sulfate groups are 1,2-trans-substituted on a cyclic pyran template. This methodology is demonstrated in an enantioselective synthesis of the trans-syn-trans fused AB cyclic ether rings of the brevetoxin natural products.

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Synthesis of trans-syn-trans Fused Bis-Pyrans via endo-Selective Cyclizations of Cyclic Sulfates. -The first examples of pyran ring formation from hydroxy-cyclic sulfate cyclization are reported. Thus, acid-catalyzed endo-regioselective cyclization of compounds (II) afford the trans-syn-trans fused

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