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

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 e...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2014-08, Vol.16 (15), p.3864-3867
Main Authors: Brady, Patrick B, Oda, Susumu, Yamamoto, Hisashi
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Ivermectin - analogs & derivatives
Ivermectin - chemical synthesis
Ivermectin - chemistry
Letter
Molecular Structure
Stereoisomerism
Trimethylsilyl Compounds - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501327g