Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions | Zendy

Patrick Brady | Zendy; Susumu Oda | Zendy; Hisashi Yamamoto | Zendy

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Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions

Author(s) -

Patrick Brady,

Susumu Oda,

Hisashi Yamamoto

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501327g

Subject(s) - aldol reaction , silylation , chemistry , stereoselectivity , diastereomer , trimethylsilyl , stereochemistry , avermectin , combinatorial chemistry , organic chemistry , catalysis , medicine , anatomy

A stereodivergent approach to the spiroketal fragment of the avermectins is described. The strategy utilizes a sequence of three aldol reactions directed by the tris(trimethylsilyl)silyl "super silyl" group. Central to this strategy is that each aldol reaction can be controlled to allow access to either diastereomer in high stereoselectivity, thereby affording 16 stereoisomers along the same linear skeleton. The aldol products can be transformed into spiroketals, including an advanced intermediate in the total synthesis of avermectin A1a.

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