In:
Angewandte Chemie, Wiley, Vol. 127, No. 6 ( 2015-02-02), p. 1774-1778
Abstract:
A type II intramolecular oxidopyrylium‐mediated [5+2] cycloaddition reaction allows the efficient and diastereoselective formation of various highly functionalized and synthetically challenging bridged seven‐membered ring systems (such as bicyclo[4.4.1] undecane, bicyclo[4.3.1]decane, bicyclo[5.4.1] dodecane, and bicyclo[6.4.1]]tridecane). This simple, thermal, direct transformation has a broad substrate scope and is high yielding, with high functional‐group tolerance and unique endo selectivity. The highly strained tricyclic cores of ingenol mebutate (picato) and cyclocitrinol are synthesized efficiently and diastereoselectively using this methodology.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.201410806
Language:
German
Publisher:
Wiley
Publication Date:
2015
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514305-6
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505872-7
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1479266-7
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506259-7
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