De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach.

De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Research Abstract Details 

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De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Abstract Text:

Miaosheng Li,George A O'Doherty,

The enantioselective synthesis of the spiroketal/macrolide natural product milbemycin beta3 has been achieved in 22 steps and 2.8% overall yield from an achiral dienoate. The spiroketal ring system was installed by three sequential asymmetric hydrations followed by sprioketalization. Both the absolute and relative stereochemistry of milbemycin beta3 was introduced by two Sharpless asymmetric dihydroxylations, two pi-allylpalladium-catalyzed reductions, and an iridium-catalyzed hydrogen migration/Claisen rearrangement to install the C-12 stereocenter.

De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Publishing Authors By Initials

M Li,GA O'Doherty,

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De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Organic letters

VOLUME: 8

Page Numbers: 3987-90

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ISSN: 1523-7060

DAY: 31

MONTH: Aug

YEAR: 2006

De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach. Information

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LANGUAGE: eng

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Grant and Affiliation Information for De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach.

AFFILIATION: Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.

Country: United States

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MEDLINETA: Org Lett

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