Construction of Pentacyclic Limonoid Skeletons via Radical Cascade Reactions

Limonoids 1 and 2 share a 6/6/6/5-membered ABCD-ring system and a six-membered oxacycle and differ in their C9-stereochemistries. A new radical-based strategy was devised to construct the pentacyclic skeletons of 1 and 2. An oxacycle-fused A-ring and enyne fragments were coupled to produce radical p...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2021-05, Vol.86 (9), p.6869-6878
Main Authors: Mutoh, Hiroyuki, Nakamura, Shu, Hagiwara, Koichi, Inoue, Masayuki
Format: Article
Language:English
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:Limonoids 1 and 2 share a 6/6/6/5-membered ABCD-ring system and a six-membered oxacycle and differ in their C9-stereochemistries. A new radical-based strategy was devised to construct the pentacyclic skeletons of 1 and 2. An oxacycle-fused A-ring and enyne fragments were coupled to produce radical precursors 4a–4c with different C7-oxygen functionalities. The bridgehead tertiary bromide of 4a–4c participated in a radical cascade reaction with the three unsaturated bonds to cyclize the C9-diastereomeric BCD-rings.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00212