Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2006-10, Vol.128 (42), p.13704-13705
Main Authors: Donohoe, Timothy J, Harris, Robert M, Burrows, Jeremy, Parker, Jeremy
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Furans - chemical synthesis
General and physical chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Osmium - chemistry
Oxidation-Reduction
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Rollinia - chemistry
Stereoisomerism
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:The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise:  the final route being just 13 linear steps and 19 chemical operations in total.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0660148