Stereochemical definition of the natural product (6R,10R,13R, 14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)‐azaspiracid‐3 by total synthesis and comparative analyses

DOI	Resolve DOI: https://doi.org/10.1002/anie.201711008
Author	Search for: Kenton, Nathaniel T.; Search for: Adu-ampratwum, Daniel; Search for: Okumu, Antony A.; Search for: Mccarron, Pearse¹; Search for: Kilcoyne, Jane; Search for: Rise, Frode; Search for: Wilkins, Alistair L.; Search for: Miles, Christopher O.¹; Search for: Forsyth, Craig J.
Affiliation	National Research Council of Canada. Measurement Science and Standards
Format	Text, Article
Abstract	The previously accepted structure of the marine toxin azaspiracid‐3 is revised based upon an original convergent and stereoselective total synthesis of the natural product. The development of a structural revision hypothesis, its testing, and corroboration are reported. Synthetic (6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R, 33R,34R,36S,37S,39R)‐azaspiracid‐3 chromatographically and spectroscopically matched naturally occurring azaspiracid‐3, whereas the previously assigned 20R epimer did not.
Publication date	2018-01-15
Publisher	Wiley
In	Angewandte Chemie International Edition 57, no. 3: 810–813.
Language	English
Peer reviewed	Yes
NPARC number	23003945
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Record identifier	04cf1117-a3ab-477f-942b-bc2129a7b5c5
Record created	2018-08-24
Record modified	2020-03-16