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. 2006 May 25;8(11):2369-72.
doi: 10.1021/ol060704z.

Total synthesis of (-)-mucocin

Affiliations

Total synthesis of (-)-mucocin

Michael T Crimmins et al. Org Lett. .

Abstract

[reaction: see text] An enantioselective total synthesis of (-)-mucocin has been completed. A combination of asymmetric glycolate aldol additions and ring closing metathesis reactions were exploited to construct the C18-C34 and C7-C17 fragments. A selective cross-metathesis reaction was employed as the key step to couple two complex fragments.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
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Scheme 3
Scheme 4
Scheme 4

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