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Issue 11, 2011
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Total synthesis of hyacinthacine A2: stereocontrolled 5-aza-cyclooctenephotoisomerization and transannular hydroamination with planar-to-point chirality transfer

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Abstract

The total synthesis of hyacinthacine A2 is reported via a novel transannular hydroamination in which planar chirality of a 5-aza-trans-cyclooctene precursor is transferred to point chirality in the product. Key to the success of this strategy was the development of a method for establishing absolute planar chirality via stereocontrolled photoisomerization of a 5-aza-cis-cyclooctene. This was accomplished by constructing a 5-aza-cis-cyclooctene precursor with a trans-fused acetonide. The improved diastereoselectivity observed upon photoisomerization of this derivative is attributed to the conformational strain of the eight-membered ring in the minor diastereomer.

Graphical abstract: Total synthesis of hyacinthacine A2: stereocontrolled 5-aza-cyclooctene photoisomerization and transannular hydroamination with planar-to-point chirality transfer

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Article information


Submitted
09 Jul 2011
Accepted
04 Aug 2011
First published
18 Aug 2011

Chem. Sci., 2011,2, 2162-2165
Article type
Edge Article

Total synthesis of hyacinthacine A2: stereocontrolled 5-aza-cyclooctene photoisomerization and transannular hydroamination with planar-to-point chirality transfer

M. Royzen, M. T. Taylor, A. DeAngelis and J. M. Fox, Chem. Sci., 2011, 2, 2162
DOI: 10.1039/C1SC00442E

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