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

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2235-2238

  McDonald, Frank E ^a,b   Vadapally, Prahlad ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BREVETOXIN; ETHER DERIVATIVE; HYDROXYL GROUP; NATURAL PRODUCT; PYRAN DERIVATIVE; SULFATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS; TRANS ISOMER;

EID: 0033583158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00214-2     Document Type: Article

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32. [15] The low yields of products 18, 20, and 22 are probably due to a combination of factors. For instance, the ruthenium-catalyzed dihydroxylations of 14 and 16 are estimated to proceed in only ca. 50% yield, in analogy to our earlier experience with similar dihydropyran substrates (ref. 10). Furthermore, compounds 17, 19, and 21 are relatively unstable and decompose upon heating in wet acetonitrile in the absence of an acid catalyst. We have not observed any evidence for exocyclization product regioisomers arising from intermediate cyclic sulfates 17 or 19. We have observed that a simple cyclic sulfate substrate arising from a trisubstituted alkene with a more distant hydroxyl group was observed to undergo pinacol-type dehydration to afford an isopropyl ketone product; X. Guo and F. E. McDonald, unpublished work.
33. 7 434.2305: found 434.2297.