Abstract:
:Ring expansion provides a powerful way of introducing a heteroatom substituent into a carbocyclic framework. However, such reactions are often limited by the tendency of a given substrate to afford only one of the two rearrangement products or fail to achieve high selectivity at all. These limitations are particularly acute when seeking to carry out late-stage functionalization of natural products as starting points in drug discovery. In this work, we present a stereoelectronically controlled ring expansion sequence towards selective and flexible access to complementary ring systems derived from common steroidal substrates. Chemical diversification of the reaction intermediate affords over 100 isomerically pure analogs with spatial and functional diversity. This regiodivergent rearrangement, and the concept of using chiral reagents to affect regiocontrol in chiral natural products, should be broadly applicable to late-stage natural product diversification programs.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Charaschanya M,Aubé Jdoi
10.1038/s41467-018-03248-2subject
Has Abstractpub_date
2018-03-05 00:00:00pages
934issue
1issn
2041-1723pii
10.1038/s41467-018-03248-2journal_volume
9pub_type
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