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Stereodivergent approach to the avermectins based on "super silyl" directed aldol reactions.

Brady PB, Oda S, Yamamoto H - Org. Lett. (2014)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.

ABSTRACT
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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1,5-Directed Aldol Reaction of 4c
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Stereodivergent approach to the avermectins based on "super silyl" directed aldol reactions.

Brady PB, Oda S, Yamamoto H - Org. Lett. (2014)

1,5-Directed Aldol Reaction of 4c
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4120983&req=5

sch3: 1,5-Directed Aldol Reaction of 4c
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.

ABSTRACT
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.

Show MeSH
Related in: MedlinePlus